Insecticidal N&#39; substituted-N-N&#39;-disubstituted-hydrazines

ABSTRACT

This invention relates to insecticidal compositions containing N&#39;-substituted-N,N&#39;-disubstitutedhydrazines, methods of using such compositions and N&#39;-substituted-N, N&#39;-disubstitutedhydrazines. Specifically, the invention relates to insect growth regulating compositions, and methods of using such compositions, which include compounds having a nucleus of the formula ##STR1## where A&#39;, B&#39;, D and J are independently any atom or group of atoms; where E is a tertiary carbon containing organic radical, a haloalkyl having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen, and is attached to the nitrogen shown in the formula by a carbon-to-nitrogen single bond; where one G 1  is C, N, O and S, and both G 2  &#39;s and the other G 1  are carbon; or one G 2  is S or P, and both G 1  &#39;s and the other G 2  are carbon; where the bonds shown as - - - are independently single or double bonds; where the A&#39;-?-G 1  and G 1  -?-B&#39; bonds are independently single bond, double bonds or aromatic bonds; where organic radical is a radical comprising at least one carbon atom, but no metal atoms; where organometallic radical is a radical containing a carbon-to-metal bond; or an agronomically acceptable salt thereof; and with the provisos discussed infra.

This application is a continuation of application Ser. No. 091,687, filed Aug. 31, 1987 which is a continuation-in-part of abandoned application Ser. No. 911,177, filed Sep. 24, 1986 which is a continuation-in-part of allowing aplication Ser. No. 789,797, filed Oct. 21, 1985, now U.S. Pat. No. 4,985,461; abandoned application Ser. No. 274,635, filed Nov. 14, 1988 which is a continuation-in-part of abandoned application Ser. No. 858,482, filed May 1, 1986, abandoned application Ser. No. 207,081, filed Jun. 15, 1988, which is a continuation-in-part of abandoned application Ser. No. 005,824, filed Feb. 4, 1987 which is a continuation-in-part of abandoned application Ser. No. 835,073, filed Feb. 28, 1986 and of abandoned a group selected from application Ser. No. 24,660, filed Mar. 11, 1987 which is a continuation-in-part application of abandoned application Ser. No. 821,187, filed Jan. 22, 1986; abandoned application Ser. No. 12,380, filed Feb. 19, 1987 which is a continuation-in-part application of abandoned application Ser. No. 885,508, filed Jul. 14, 1986; and abandoned application Serial No. 911,928, filed Sep. 26, 1986 which are incorporated by reference.

BACKGROUND OF THE INVENTION

This invention relates to N'-substituted-N,N'-disubstitutedhydrazines, which are useful as insecticides, compositions containing those compounds and methods of their use. More particularly, the invention relates to

The search for compounds which have a combination of excellent insecticidal activity and low undesirable toxicity is a continuing one because of factors such as the desire for compounds exhibiting greater activity, better selectivity, low undesirable environmental impact, low production cost and effectiveness against insects resistant to many known insecticides.

Compounds of the present invention are particularly suitable for controlling plant-destructive insects in crops of cultivated plants, ornamentals and forestry.

Certain hydrazine derivatives have been disclosed in the literature. However, none of the prior art literature suggests hydrazines derivatives having insect growth regulating characteristics.

U.S. Pat. No. 3,481,972 discloses 2-(betahydroxyethyl)-2-methyl acid hydrazine compounds of the formula ZC(O)NHN(CH₃)CH₂ CH₂ OH where Z represents furyl, cyclohexyl, phenyl, benzyl, styryl, dihydrostyryl or substituted phenyl. The compounds are stated to be useful as pesticides for the control of such organisms as insects, arachnids, nematodes, fungi, plants and helminth organisms.

U.S. Pat. No. 4,062,934 discloses compounds of the formula ##STR2## where R₃ and R₄ represent a hydrogen atom or a one to four alkyl and n is an integer from zero to four. These compounds are used as X-ray contrast media.

U.S Pat. No. 4,189,482 discloses compounds of the formula ##STR3## where R₃ is lower alkyl, or substituted or unsubstituted phenyl, benzyl, phenethyl, thienyl or furyl; R₄ is hydrogen or lower alkyl; ##STR4## as intermediates to penicillins having an imino substituted piperazindioncarbonylamino aceyl side chains.

U.S. Pat. No. 4,317,741 discloses a poly(oxyalkylated)hydrazine of the formula ##STR5## where R is hydrogen, (C₁ -C₄)alkyl, phenyl or mixtures thereof and the sum of w, x, y and z is from about four to about 20. These compounds are used as corrosion inhibitors.

U.S. Pat. No. 4,357,351 discloses five specific compounds (Compound Nos. 400 and 402-404) of the formula ##STR6## where n averages 7.7 and n' averages 11. These compounds are disclosed to have leptericidal activity. However, they are not claimed and it is not seen how these five compounds are included in the generic formula disclosed in the patent.

U.S. Pat. No. 4,547,524 discloses a class of benzoyl hydrazone derivatives which have insecticidal activity. However, the unsaturated carbon is bonded to hydrogen, lower alkyl, or phenyl, or forms part of a cyclohexane ring. Further the N'-substituent is not taught to include a tertiary carbon atom.

U.S. Pat. No. 4,564,611 discloses (di)thiophosphoric and -phosphonic acid derivatives having the formula ##STR7## in which R denotes (C₁ -C₄)-alkyl; R₁ denotes (C₁ -C₄)-alkyl, (C₁ -C₄)-alkoxy, (C₁ -C₄)-alkylmercapto, (C₁ -C₄)-alkylamino or di(C₁ -C₄)alkylamino; R₂ and R₃ independently of one another denote hydrogen, (C₁ -C₄)-alkyl, (C₅ -C₆)-cycloalkyl, benzyl or furylmethyl; R₄ denotes (C₁ -C₄)-alkyl, (C₁ -C₃)-alkoxymethyl, (C₁ -C₃)-alkylmercaptomethyl or phenyl and X denotes oxygen or sulfur, which have activity against sucking and biting insects, acarides and nematodes, and display good fungicidal activity. Insect growth regulating activity is not disclosed. Further, R₂ is not taught to include a tertiary carbon.

The Chemical Abstracts citation CA 84(21):150168j indicates that Azerb Khim Zh, 1975, (5), 47-8 discloses Me₂ CHCH₂ CH═NN(Ac)CH₂ CH₂ OH, PhCH═NN(Ac)CH₂ CH₂ OH and Me₂ CHCH═NN(Ac)CH₂ CH₂ OH which have pesticidal activity.

In 88 J.A.C.S, 4677-4681 (1966) N'-t-butyl-N'-methylcarbonyl-N-benzoylhydrazine is disclosed. No biological activity is disclosed.

In 37 Tetrahedron Letters, 3575-3578 (1979), the result of an electron spin resonance study is reported. The hydrazyl radicals produced included PhC(O)N(t-Bu)NC(O)Ph and PhC(O)N(Et₃ Si)NC(O)Ph. No utility was suggested for the radicals which were studied.

In 25 Aust. J. Chem., 523-529 (1972), several N,N'-dibenzoylhydrazine derivatives are disclosed including (3-methylbutyl)-; N'-benzyl- and N'-phenyl-N,N'-dibenzoylhydrazine in which one or both nitrogen atoms are alkylated or phenylated. No biological activity is disclosed for those compounds.

In 61 Helv. Chim. Acta, 1477-1510 (1978), several N,N'-dibenzoylhydrazine and hydrazide derivatives including N'-t-butyl-N-benzoyl-N'-(4-nitrobenzoyl)hydrazine are disclosed. No biological activity is disclosed for those compounds.

In 44 J.A.C.S., 2556-2567 (1922), isopropylhydrazine (CH₃)₂ CH--NH--NH₂, symmetrical diisopropylhydrazine, dibenzoylisopropylhydrazine and certain derivatives are disclosed. No biological activity is disclosed for those compounds.

In 44 J.A.C.S., 1557-1564 (1972), isopropyl, methyl and bornyl semicarbazides are disclosed. No biological activity is disclosed for those compounds.

In 48 J.A.C.S., 1030-1035 (1926), symmetrical di-methylphenylmethylhydrazine and certain related compounds including 1,2-bis-methylphenylmethyl-4-phenylsemicarbazide are disclosed. No biological activity is disclosed for those compounds.

In 27 Bull. Chem. Soc. Japan, 624-627 (1954), certain hydrazine derivatives including alpha,beta-dibenzoylphenylhydrazine are disclosed. No biological activity is disclosed for those compounds.

In J. Chem. Soc. (C), 1531-1536 (1966), N,N'-dibenzoylphenylhydrazine and N-acetyl-N'-benzoyl-p-nitrophenylhydrazine are disclosed. No biological activity is disclosed for those compounds.

In 56B Chem. Berichte, 954-962 (1923), symmetrical di-isopropylhydrazines, symmetrical diisobutyl- and certain derivatives including N,N'-diisobutyldibenzoylhydrazine are disclosed. No biological activity is disclosed for those compounds.

In 590 Annalen der Chemie, 1-36 (1954), certain N,N'-dibenzoylhydrazine derivatives are disclosed including N'-methyl- and N'-(2-phenyl)-isopropyl-N,N'-dibenzoylhydrazine. No biological activity is disclosed for those compounds.

In J. Chem. Soc., 4191-4198 (1952), N,N'-di-n-propylhydrazine, N,N'-dibenzoylhydrazine and bis-3,5-dinitrobenzoyl are disclosed. No biological activity is disclosed for those compounds.

In 32 Zhur. Obs. Khim., 2806-2809 (1962), N'-2,4-methyl-2,4-pentadiene-N,N'-dibenzoylhydrazine is disclosed. No biological activity is disclosed.

In 17 Acta. Chim. Scand., 95-102 (1963), 2-benzoyloylhydrazide (C₆ H₅ --CS--NHNH--CO--C₆ H₅) and certain hydrazone and hydrazine derivatives are disclosed including 1,2-dibenzoyl-benzylhydrazine. No biological activity is disclosed for those compounds.

In 25 Zhur. Obs. Khim, 1719-1723 (1955), N,N'-biscyclohexylhydrazine and N,N'-dibenzoylcyclohexylhydrazine are disclosed. No biological activity is disclosed for those compounds.

In J. Chem. SOc., 4793-4800 (1964), certain dibenzoylhydrazine derivatives are disclosed including tribenzoylhydrazine and N,N'-dibenzoylcyclohexylhydrazine. No biological activity is disclosed for those compounds.

In 36 J. Prakt. Chem., 197-201 (1967), certain dibenzoylhydrazine derivatives including N'-ethyl-; N'-n-propyl-; N'-isobutyl-; N'-neopentyl-; N'-n-heptyl-; and N'-cyclohexylmethyl-N,N'-dibenzoylhydrazines are disclosed. No biological activity is disclosed for those compounds.

In 26 J.O.C., 4336-4340 (1961) N'-t-butyl-N,N'-di-(t-butoxycarbonyl)hydrazide is disclosed. No biological activity is disclosed.

In 41 J.O.C., 3763-3765 (1976), N'-t-butyl-N-(phenylmethoxycarbonyl)-N'-(chlorocarbonyl)hydrazide is disclosed. No biological activity is disclosed.

In 94 J.A.C.S., 7406-7416 (1972) N'-t-butyl-N,N'-dimethoxycarbonylhydrazide is disclosed. No biological activity is disclosed.

In 43 J.O.C., 808-815 (1978), N'-t-butyl-N-ethoxycarbonyl-N'-phenylaminocarbonylhydrazide and N'-t-butyl-N-ethoxycarbonyl-N'-methylaminocarbonylhydrazide are disclosed. No biological activity is disclosed for those compounds.

In 39 J. Econ. Ent., 416-417 (1946), certain N-phenyl-N'-acylhydrazines are disclosed and evaluated for their toxicity against codling moth larvae.

Compounds of the present invention are distinguished by their excellent insecticidal activity, particularly against insects of the orders Lepidoptera and Coleoptera, and most particularly by their insect growth regulating activity without material adverse impact on beneficial insects.

SUMMARY OF THE INVENTION

In accordance with the present invention, there are provided novel insect growth regulating compositions including compounds having the formula: ##STR8## where one G₁ is C, N, O or S, and both G₂ 's and the other G₁ are carbon; or one G₂ is S or P, and both G₁ 's and the other G₂ are carbon; where the bond shown as -- is a single or double bond: or an agronomically acceptable salt thereof.

The invention also relates to compounds having the nucleus of the formula ##STR9## where N is nitrogen; where A', B', D and J are independently any atom or group of atoms; where E is a tertiary carbon containing organic radical, a haloalkyl having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen, and is attached to the nitrogen shown in the formula by a carbon-to-nitrogen single bond; where one G₁ is carbon, nitrogen, oxygen or sulfur, and both G₂ 's and the other G₁ are carbon; or one G₂ is sulfur or phosphorus, and both G₁ --s and the other G₂ are carbon; where the bonds shown as -- are independently single or double bonds; provided that when the G₂ adjacent D is carbon or phosphorus, one of D--G₂ and G₂ --N is a double bond the other is a single bond; provided that when the G₂ adjacent D is sulfur, D--G₂ is a double bond and G₂ --N is a single bond; where the A'-?-G₁ and G₁ -?-B' bonds are independently single bond, double bonds or aromatic bonds; provided that the D--G₂ bond is other than a carbon-to-carbon or hydrogen-to-carbon single bond; provided that the J--G₂ bond is a double bond or a hydrogen-to-carbon single bond; provided that at least one of A' and B' is other than hydrogen when the D--G₂ bond is a double bond; provided that A' comprises at least two non-hydrogen atoms when the G₁ adjacent A' is a carbon; provided that B' is other than a hydrogen atom when the G₁ adjacent B' is a carbon; provided that E is not a straight chain alkyl, --CH₂ CH₂ N(CH₂ CH₃)₂, cyclohexyl, a six-membered cyclic containing organic radical, a cyclic aromatic radical, or an organic radical containing ##STR10## provided that E is not a sulfur or oxygen containing organic radical; provided that E does not have a chain length of non-hydrogen atoms greater than five; provided that when A'-?-G₁ and G₁ -?-B' are phenyl, and J--G₂ are carbonyl and hydrogen is bonded to the nitrogen adjacent the D--G₂, E is not neopentyl; provided that when A'-?-G₁ is phenyl, D--G₂ and J--G₂ are carbonyl, hydrogen is bonded to the nitrogen adjacent the D--G₂ and E is t-butyl, G₁ -?-B' is not 4-nitrophenyl; where organic radical is a radical comprising at least one carbon atom, but no metal atoms; and where organometallic radical is a radical containing a carbon-to-metal bond; or an agronomically acceptable salt thereof.

The invention also relates to a method of regulating insect growth which comprises contacting insects with a compound having the nucleus of the formula ##STR11## where one G₁ is carbon, nitrogen, oxygen or sulfur, and both G₂ 's and the other G₁ are carbon; or one G₂ is sulfur or phosphorus, and both G₁ 's and the other G₂ are carbon; where the bond shown as -- is a single or double bond; or an agronomically acceptable salt thereof.

DETAILED DESCRIPTION OF THE INVENTION

The term "halo" should be understood as including chloro, fluoro, bromo and iodo. The term "alkyl" by itself or as a part of another substituent, unless otherwise stated, includes straight or branched chain groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, isobutyl, neopentyl and the like and where indicated higher homologues and isomers such as n-octyl, isooctyl and the like. The term "haloalkyl" by itself or as part of another substituent is an alkyl group of the stated number of carbon atoms having one or more halo atoms bonded thereto such as chloromethyl, 1- or 2-bromoethyl, trifluoromethyl and the like. Analogously, "cyanoalkyl" by itself or as part of another group is an alkyl group of the stated number of carbon atoms having one or more cyano groups bonded thereto; "haloalkoxy" by itself or as part of another group is an alkoxy group of the stated number of carbon atoms having one or more halo atoms bonded thereto such as difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy and the like. "Alkenyl" and "alkynyl" by themselves or as part of another substituent comprise straight and branched chain groups of the stated number of carbon atoms. "Alkadienyl" is a straight or branched chain alkenyl group comprising two carbon-to-carbon double bonds that can be conjugated such as 1,3-butadienyl, cumulated such as 1,2-propadienyl or isolated such as 1,4-pentadienyl.

The term "organic radical" should be understood to mean a radical comprising at least one carbon atom but no metal atoms. Examples of organic radicals include alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocycles, esters, ethers, thio derivatives and amine derivatives.

The term "organometallic radical" should be understood to include radicals containing a carbon-to-metal bond. Examples of such radicals include trimethylsilyl.

The term "tertiary carbon" is meant to refer to a carbon having at least three carbon-to-carbon single bonds.

The term "aryl" should be understood to include those molecules which have a ring structure characteristic of benzene, naphthalene, phenanthrene and anthracene, that is either the six-carbon ring of benzene or the condensed six-carbon rings of other aromatic derivatives. Examples of aryl radicals include unsubstituted and substituted phenyl, benzyl and naphthalene.

The term "cyclic aromatic radical" should be understood to mean unsaturated cyclic compounds including heterocyclic compounds. Examples of cyclic aromatic radicals include aryl, indolyl, thienyl, furyl, pyrrolyl, triazolyl and tetrazolyl.

Representative examples of six-membered heterocycles having one, two, three or four nitrogen atoms and two to five nuclear carbon atoms include 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 5-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 3-pyrazinyl, 2-(1,3,5-triazinyl), 3-(1,2,4-triazinyl), 5-(1,2,4-triazinyl), 6-(1,2,4-triazinyl), 4-(1,2,3-triazinyl) and 5-(1,2,3-triazinyl).

Representative examples of five-membered heterocycles include 2-furyl; 3-furyl; 2-thienyl; 3-thienyl; 4-(1,2,3-triazolyl); 3-(1,2,4-triazolyl); 5-(1,2,4-triazolyl), 2-pyrrolyl; 2-oxazolyl; and the like.

Those N'-substituted-N,N'-diacylhydrazines of Formula I which possess acidic or basic functional groups may be further reacted to form novel salts with appropriate bases or acids. These salts also exhibit pesticidal activity. Typical salts are the agronomically acceptable metal salts, ammonium salts and acid addition salts. Among the metal salts are those in which the metal cation is an alkali metal cation such as sodium, potassium, lithium or the like; alkaline earth metal cation such as calcium, magnesium, barium, strontium or the like; or heavy metal cation such as zinc, manganese, cupric, cuprous, ferric, ferrous, titanium, aluminum or the like. The ammonium salts include those in which the ammonium cation has the formula NR⁵ R⁶ R⁷ R⁸ wherein each of R⁵, R⁶, R⁷ and R⁸ are independently hydrogen, hydroxy, (C₁ -C₄)alkoxy, (C₁ -C₂₀)-alkyl, (C₃ -C₈)alkenyl, (C₃ -C₈)alkynyl, (C₂ -C₈)hydroxyalkyl, (C₂ -C₈)alkoxyalkyl, (C₂ -C₆)aminoalkyl, (C₂ -C₆)haloalkyl, amino, (C₁ -C₄)alkyl- or (C₁ -C₄)dialkylamino, substituted or unsubstituted phenyl, substituted or unsubstituted phenylalkyl, having up to four carbon atoms in the alkyl moiety, or any two of R⁵, R⁶, R⁷ or R⁸ can be taken together to form with the nitrogen atom a 5- or 6-membered heterocyclic ring, optionally having up to one additional hetero atom (e.g., oxygen, nitrogen, or sulfur) in the ring, and preferably saturated, such as piperidino, morpholino, pyrrolidino, piperazino or the like, or any three of R⁵, R⁶, R⁷ or R⁸ can be taken together to form with the nitrogen atom a 5- or 6-membered aromatic heterocyclic ring, such as piperazole or pyridine. When R⁵, R⁶, R⁷ or R⁸ substituent in the ammonium group is a substituted phenyl or substituted phenylalkyl, the substituents on the phenyl and phenalkyl will generally be selected from halo, (C₁ -C₈)alkyl, (C₁ -C₄)alkoxy, hydroxy, nitro, trifluoromethyl, cyano, amino, (C₁ -C₄)alkylthio and the like. Such substituted phenyl groups preferably have up to two such substituents. Representative ammonium cations include ammonium, dimethylammonium, 2-ethylhexylammonium, bis(2-hydroxyethyl)ammonium, tris(2-hydroxyethyl)ammonium, dicyclohexylammonium, t-octylammonium, 2-hydroxyethylammonium, morpholinium, piperidinium, 2-phenethylammonium, 2-methylbenzylammonium, n-hexylammonium, triethylammonium, trimethylammonium, tri(n-butyl)-ammonium, methoxyethylammonium, diisopropylammonium, pyridinium, dialkylammonium, pyrazolium, propargylammonium, dimethylhydrazinium, octadecylammonium, 4-dichlorophenylammonium, 4-nitrobenzylammonium, benzyltrimethylammonium, 2-hydroxy-ethyldimethyloctadecylammonium, 2-hydroxyethyldiethyloctylammonium, decyltrimethylammonium, hexyltriethylammonium, 4-methylbenzyltrimethylammonium, and the like. Among the acid addition salts are those in which the anion is an agronomically acceptable anion such as hydrochloride, hydrobromide, sulfate, nitrate, perchlorate, acetate, oxalate and the like.

For insects to successfully grow, that is progress from one larval stage to the next larger larval stage or metamorphose to an adult stage, they must moult or shed the old cuticle. Compounds of this invention are insect growth regulators in that they interfere with this natural moulting and other growth-regulated processes.

Growth regulatory effects are not usually expressed rapidly after treatment. This is contrary to conventional insecticides, such as neurotoxins, respiratory poisons and the like, which affect vital processes and which are noted for rapidity of effect.

For example, compounds such as: (R¹)₂ --P(X)X(CH₂)_(n) C(O)NHN(R")C(O)C₅ H₆, where

R¹ =lower alkyl, alkoxy, thioalkyl and may be identical or different

X=0 or S, n=0-5 and R"=t-butyl

would constitute conventional, fast-acting, cholinesterese-inhibiting neurotoxins with efficacy anticipated against a comparatively broad range of insect orders and acarides as well as non-target organisms such as mammals, fish and birds. By contrast insect growth regulators as claimed herein would be somewhat less rapid in effect with activity being confined to particular insects which are largely pestiferous and including those strains resistant to organophosphate insecticides. Although somewhat slower to act than conventional cholinesterese-inhibiting neurotoxins, compounds of this invention are sufficiently rapid-acting so as to protect agricultural crops and are therefore superior to other known insect growth regulators which are quite slow to elicit effects.

The present inventors have found that the following parameters are important to yield compounds having the nucleus of Formula Ia which are insect growth regulators. At least one of the moieties attached to one of the G₁ 's should have at least some bulk, i.e., at least two or three non-hydrogen atoms. However, if the bulk becomes too great, the compounds become less effective as insect growth regulators. Therefore, the moieties attached to the G₁ 's should be no greater than about 21 non-hydrogen atoms.

The size of the moiety E of Formula I is important. E should have at least 4 non-hydrogen atoms. Oxygen containing radicals have been found to be generally not preferred. If oxygen is present, generally E should be bulkier. Moieties containing two oxygen atoms or one oxygen and one sulfur atom are less preferred. It is preferred that E have no greater than 10 non-hydrogen atoms. Preferably, E does not include a chain of greater than four or five non-hydrogen atoms but is highly branched.

The size of the radical D and any moiety attached to the nitrogen adjacent to G₂ --D of Formula I are found to be less important.

The compounds of this invention or their precursors can be prepared according to the following processes. Process A can be used when preparing compounds according to Formula II below where X and X' are both oxygen and A and B are the same (for example, both A and B are phenyl or 4-chlorophenyl) or different (for example, A is 4-methylphenyl and B is 4-chlorophenyl). ##STR12## wherein

A and B are organic radicals attached to the carbon shown in Formula II by a carbon-to-carbon single bond and R¹ is other than hydrogen. ##STR13## where R¹, A and B are as defined above for Formula II and X and X' are oxygen.

When R¹ is cyano substituted alkyl the intermediate Va may be made as follows: ##STR14## where M is K or Na, X and X' are oxygen, A and B are as defined above for Formula II, and R₃ and R₄ are the same or different hydrogen or (C₂ -C₉) straight or branched chain unsubstituted or substituted alkyl having one or two of the same or different (C₃ -C₆)cycloalkyl; Process B can be used when preparing compounds according to Formula II where X and X' are oxygen, and R¹, A and B are as defined above for Formula II. ##STR15## where X and X' are oxygen, A and B are as defined above for Formula II, and R³ and R⁴ are the same or different hydrogen or (C₂ -C₉) straight or branched chain unsubstituted or substituted alkyl having one or two of the same or different (C₃ -C₆)cycloalkyl. As can be seen above, the intermediate product of Step 2, the compounds of Formula X, corresponds to the compounds of Formula V. In addition, the compound of Formula XI corresponds to the compounds of Formula II where X and X' are oxygen. ##STR16## where R¹, A and B are as defined above for Formula II and W is a good leaving group such as halo, for example, chloro; an alkoxy, for example, ethoxy; methyl sulfonate (--OSO₂ CH₃); or an ester, for example, acetate (--OC(O)CH₃).

Process C can be used when preparing compounds according to Formula II where A, B and R¹ are as defined for Formula II and one or both X and X' are sulfur. ##STR17## where A, B and R¹ are as defined above for Formula II and one or both X and X' are sulfur, and Y is a good leaving group such as carboxyalkylthio (for example, carboxymethylthio, --SCH₂ CO₂ H); alkylthio (for example, methylthio); or halo (for example, chloro).

Process D can be used when preparing compounds according to Formula II where X and X' are oxygen and R¹, A and B are as defined above for Formula II. ##STR18## wherein A, B and R¹ are as defined above for Formula II and Z is t-butyl; ethyl; phenyl; or benzyl.

The starting materials for each process are generally commercially available, or can be prepared by generally customary and known methods.

Other compounds of this invention or their precursors can be prepared by reacting a suitably substituted hydrazine (Formula II) with an alkyl halide, allyl halide or phenylmethylhalide in the presence of a base in an inert or substantially inert solvent or mixture of solvents according to the following process: ##STR19## where X, X', R¹, R², A and B are as defined above for Formula II and Hal is halogen (chloro, fluoro or bromo).

Suitable bases for use in the above process include metal hydrides such as sodium hydride or potassium hydride; metal alkoxides such as sodium alkoxides or potassium alkoxides; sodium hydroxide; potassium hydroxide; or lithium diisopropyl amide. If desired, mixtures of these bases may be used. The preferred base is potassium t-butoxide.

Suitable solvents for use in the above process include ethers such as tetrahydrofuran (THF), glyme and the like; dimethylformamide (DMF); dimethylsulfoxide (DMSO); acetonitrile; or a mixture of water and benzene or toluene. If desired, mixtures of these solvents may be used. The preferred solvent is dimethylformamide.

The above process can be carried out at temperatures between about --20° C. and about 100° C. Preferably, this reaction is carried out between about -5° C. and about 50° C.

Preparation of the compounds of the present invention by the above process is preferably carried out at about atmospheric pressure although higher or lower pressures can be used if desired.

Substantially equimolar amounts of reactants are preferably used although higher or lower amounts can be used if desired.

Generally one equivalent of base is used per equivalent of starting material of Formula XXI.

The compounds of Formula XXI are generally commercially available or can be prepared by known procedures.

Modifications to the above process may be necessary to accommodate reactive functionalities of particular substituents. Such modifications would be apparent and known to those skilled in the art.

In process A, a compound of Formula III is reacted with a monosubstituted hydrazine of Formula IV or a corresponding acid addition salt such as the hydrochloride salt or the like in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford an intermediate product of Formula V which can be isolated or further reacted with a compound of Formula VI in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula II.

When A and B are the same, for example, both A and B are 4-chlorophenyl, two equivalents of a compound of Formula III or VI are reacted with a monosubstituted hydrazine of Formula IV in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula II.

Examples of the compounds of Formula III and/or Formula VI which can be used in the above processes include benzoyl chloride, 4-chlorobenzoyl chloride, 4-methylbenzoyl chloride, 3,5-dichlorobenzoyl chloride, 2-bromobenzoyl chloride, 3-cyanobenzoyl chloride, 3-toluoyl chloride, 4-toluoyl chloride, 4-ethylbenzoyl chloride, 2-nitrobenzoyl chloride, 2,3-dimethylbenzoyl chloride, 2-nitro-5-toluoyl chloride, cyclohexylcarbonyl chloride, n-butanoyl chloride, n-pentanoyl chloride, phenylacetyl chloride, 1-cyclohexenecarbonyl chloride, pivaloyl chloride, trichloroacetyl chloride, methacryloyl chloride and the like. The compounds of Formula III and/or Formula VI are generally commercially available or can be prepared by known procedures.

Examples of the compounds of Formula IV which can be used in the above processes include isopropylhydrazine, t-butylhydrazine, neopentylhydrazine, alpha-methylneopentylhydrazine, isobutylhydrazine, isopentylhydrazine, isooctylhydrazine, 1,1-dimethyl-3-butenylhydrazine, (trimethylsilylmethyl)hydrazine, (1,1,1-trifluoro-2-propyl)hydrazine, (2,2,2-trifluoroethyl)hydrazine, (1-cyano-1-methyl)ethylhydrazine and the like. The compounds of Formula IV are generally commercially available or can be prepared by known procedures. For example, the Grignard reagent addition product of acetone azine in diethyl ether is hydrolyzed by the addition of an acid (such as oxalic acid), in a suitable solvent or mixture of solvents (such as ethanol and diethyl ether, 1:1) to afford the monosubstituted hydrazine of Formula IV.

Suitable solvents for use in the above processes include water; alcohols such as methanol, ethanol, isopropanol and the like; hydrocarbons such as toluene, xylene, hexane, heptane and the like; glyme; tetrahydrofuran; acetonitrile; pyridine; or haloalkanes such as methylene chloride or mixtures of these solvents.

Preferred solvents are water, toluene, methylene chloride or a mixture of these solvents.

Examples of bases for use in the above processes include tertiary amines such as triethylamine; pyridine; potassium carbonate; sodium carbonate; sodium bicarbonate; sodium hydroxide; or potassium hydroxide. Preferred bases are sodium hydroxide, potassium hydroxide or triethylamine.

In Process B, Method 1, a compound of Formula VII is reacted with a ketone or aldehyde of Formula VIII in an inert or substantially inert solvent or mixture of solvents and optionally in the presence of a catalyst to afford an intermediate product of Formula IX. The intermediate product of Formula IX is then further reacted with a reducing agent in an inert or substantially inert solvent or mixture of solvents to afford a second intermediate product of Formula X which can be isolated or further reacted with a compound of Formula VI in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula XI.

Examples of the compounds of Formula VII which can be used in the above Process B, Method 1, include benzoylhydrazine, 4-chlorobenzoylhydrazine, 2-methylbenzoylhydrazine, 4-methylbenzoylhydrazine, 3,5-dichlorobenzoylhydrazine and the like. The compounds of Formula VII are generally commercially available or can be prepared by known procedures.

Examples of the compounds of Formula VIII which can be used in the above Process B, Method 1, include 1,1,1-trimethylacetaldehyde, methylethylketone, diethylketone, trifluoroacetone, methacrolein, ethyl pyruvate and the like. The compounds of Formula VIII are generally commercially available or can be prepared by known procedures.

Optionally, a catalyst may be used in Step 1, Method of of Process B. Suitable catalysts generally include organic acids such as acetic acid, trifluoroacetic acid, oxalic acid and the like; mineral acids such as hydrochloric acid, sulfuric acid, nitric acid and the like; arylsulfonic acids such as toluenesulfonic acid; or pyridinium toluenesulfonate. Preferred catalysts are organic acids or arylsulfonic acids. Most preferred catalysts are acetic acid or trifluoroacetic acid.

Suitable solvents for use in the above Process B, Method 1, Step 1, include alcohols such as methanol, ethanol, isopropanol and the like; hydrocarbons such as toluene, benzene; ethers such as tetrahydrofuran (THF), glyme and the like; or dimethylformamide. Preferred solvents are alcohols and hydrocarbons. Most preferred solvents are alcohols such as methanol or ethanol.

Examples of suitable reducing agents for use in the above Process B, Method 1, Step 2, include hydrides such as sodium borohydride and derivatives thereof such as sodium cyanoborohydride, lithium aluminum hydride and derivatives thereof and the like; or diborane. Preferred reducing agents are sodium borohydride and derivatives thereof or lithium aluminum hydride and derivatives thereof. Most preferred as reducing agents are borane and diborane.

Optionally, in Process B, Method 1, Step 2, a catalyst may be included. Examples of suitable catalysts include organic acids such as acetic acid, trifluoroacetic acid; or mineral acids such as hydrochloric acid, sulfuric acid and the like. Preferred catalysts are organic acids or hydrochloric acid. Most preferred catalysts are acetic acid, trifluoroacetic acid or hydrochloric acid.

Suitable solvents for use in the above Process B, Method 1, Step 2, include alcohols such as methanol, ethanol, isopropanol and the like; ethers such as tetrahydrofuran (THF), diethylether, glyme and the like; or halohydrocarbons such as methylene chloride, chloroform and the like. Preferred solvents are alcohols and most preferred are methanol or ethanol.

Step 3 of Process B, Method 1 corresponds to Step 2 of Process A. Consequently, those bases and solvents suitable for use in Step 2 of Process A are suitable for use in Step 3, Method 1 of Process B including the preferred bases and solvents described above.

In Process B, Method 2, N'-substituted-N'-benzoylhydrazine of Formula XIII or N'-substituted-N-benzoylhydrazine of Formula XIIIa is reacted with a compound of Formula XII in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula II.

The compounds of Formula XII are generally commercially available or can be prepared from commercially available compounds by procedures well known to those skilled in the art as described below.

Examples of the compounds of Formula XIII which can be used in the above Process B, Method 2, include N'-t-butyl-N'-benzoylhydrazine; N'-t-butyl-N'-(3-methylbenzoyl)hydrazine; N'-t-butyl-N'-(4-chlorobenzoyl)hydrazine; N'-t-butyl-N'-(2-fluorobenzoyl)hydrazine; N'-isopropyl-N'-benzoylhydrazine; N'-neopentyl-N'-(4-chlorobenzoyl)hydrazine, N'-isopropyl-N-benzoylhydrazine; N'-sec-butyl-N-benzoylhydrazine; N'-(1-methyl)neopentyl-N-benzoylhydrazine; N'-neopentyl-N-benzoylhydrazine; N'-isobutyl-N-benzoylhydrazine; N'-(1,2,2-trimethylpropyl)-N-benzoylhydrazine; N'-diisopropylmethyl-N-benzoylhydrazine; N'-t-butyl-N-benzoylhydrazine; N'-t-butyl-N-(4-methylbenzoyl)hydrazine; N'-t-butyl-N-(4-chlorobenzoyl)hydrazine; N'-(1,1-dimethyl-3-butenyl)-N'-benzoylhydrazine, N'-(trimethylsilylmethyl)-N'-(4-methylbenzoyl)hydrazine, N'-(1,1,1-trifluoro-2-propyl)-N'-(2,4-dichlorobenzoyl)hydrazine, N'-(1-cyano-1-methyl)ethyl-N'-(2-methylbenzoyl)hydrazine and the like.

Suitable solvents for use in the above Prccess B, Method 2, include water; hydrocarbons such as toluene, xylene, hexane, heptane and the like; alcohols such as methanol, ethanol, isopropanol, and the like; glyme; tetrahydrofuran; acetonitrile; pyridine; or haloalkanes such as methylene chloride; or mixtures of these solvents. Preferred solvents are water, toluene, methylene chloride or a mixture of these solvents.

Examples of bases suitable for use in the above Process C includes tertiary amines such as triethylamine; pyridine; potassium carbonate; sodium carbonate; sodium bicarbonate; sodium hydroxide; or potassium hydroxide. Preferred bases are sodium hydroxide, or triethylamine.

The compounds of Formula XII are commercially available, such as nicotinoyl chloride hydrochloride, isonicotinoyl chloride hydrochloride and ethyl picolinate or can be prepared from commercially available materials by procedures known to those skilled in the art.

The compounds of Formula XIII can be prepared by procedures known to those skilled in the art from commercially available reactants. By way of example, a suitably substituted hydrazine (such as t-butyl-hydrazine or (1,1,1-trifluoro-2-propyl)hydrazine) is reacted with an aldehyde or ketone (such as acetone) in the presence of a base (such as triethylamine) to afford a hydrazone which is then reacted with a benzoyl chloride in an inert or substantially inert solvent or mixture of solvents in the presence of a base (such as sodium hydroxide) to afford an N'-substituted-N'-benzoylhddrazone which is then reacted with an acid (such as hydrochloric acid) to afford the compound of Formula XIII. Alternatively, a suitable substituted hydrazine (such as t-butyl-hydrazine or (trimethylsilylmethyl)hydrazine) is reacted with di-tertbutyldicarbonate in an inert or substantially inert solvent or mixture of solvents (such as toluene/water) to afford an N'-t-butyl-N-t-butoxycarbonylhydrazine or an N'-(trimethylsilylmethyl)-N-t-butoxycarbonylhydrazine which is then reacted with a benzoylchloride in an inert or substantially inert solvent or mixture of solvents to afford N'-t-butyl-N'-benzoyl-N-t-butoxy-carbonylhydrazine or an N'-(trimethylsilylmethyl)-N'-benzoyl-N-t-butoxycarbonylhydrazine which is then reacted with an acid to afford the desired compound of Formula XIII.

In Process C, a compound of Formula XIV is reacted with a monosubstituted hydrazine of Formula IV or a corresponding acid addition salt such as the hydrochloride salt or the like in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford an intermediate compound of Formula XV which can be isolated or further reacted with a compound of Formula XVI in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula I.

In Process D, a monosubstituted hydrazine of Formula IV or a corresponding acid addition salt, such as the hydrochloride salt or the like, is reacted with a compound of Formula XVII in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford an intermediate product of Formula XVIII. The intermediate product of Formula XVIII is then further reacted with a compound of Formula VI in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford a second intermediate product of Formula XIX. The second intermediate product of Formula XIX is then further reacted with an acid in an inert or substantially inert solvent or mixture of solvents to afford a third intermediate product of Formula XX. The third intermediate product of Formula XX is then further reacted with a compound of Formula III in the presence of a base in an inert or substantially inert solvent or mixture of solvents to afford the desired product of Formula II.

Examples of the compounds of Formula XVII which can be used in the above Process D include di-t-butyldicarbonate, diethyldicarbonate, diphenyldicarbonate, dibenzyldicarbonate and the like. The compounds of Formula XVII are generally commercially available or can be prepared by known procedures.

Suitable solvents for use in the above Process D, Steps 1, 2 and 4 include water; tetrahydrofuran; dioxane; toluene; alcohols such as methanol, ethanol and isopropanol; hexane; acetonitrile; pyridine; and haloalkanes such as methylene chloride; or mixtures of these solvents.

Preferred solvents are dioxane; toluene; tetrahydrofuran; pyridine; methylene chloride or water.

Most preferred solvents are dioxane; water or toluene.

Examples of the bases for use in the above Process D, Steps 1, 2 and 4 include tertiary amines such as triethylamine; pyridine; potassium carbonate, sodium carbonate; sodium bicarbonate; sodium hydroxide; and potassium hydroxide.

Preferred bases are sodium hydroxide; potassium hydroxide; pyridine or triethylamine.

Suitable solvents for use in the above Process D, Step 3 include alcohols such as methanol, ethanol and isopropanol; water; tetrahydrofuran; dioxane; and acetonitrile.

Preferred solvents are methanol or ethanol.

Examples of acids for use in the above Process D, Step 3 include concentrated hydrochloric acid or concentrated sulfuric acid.

When A and B are the same, for example, both A and B are unsubstituted phenyl, two equivalents of a compound Formula XIV or XVI are reacted with a monosubstituted hydrazine of Formula IV in the presence of a base in an inert or substantially inert solvent or mixure of solvents to afford the desired product of Formula II.

Examples of the compounds of Formula XIV and/or Formula XVI which can be used in the above Process C include 3-methyl-methylthio-thiobenzoate, 4-chloromethylthio-thiobenzoate, 4-methyl-methylthio-thiobenzoate, carboxymethylthio-thiobenzoate and the like. The compounds of Formula XIV and/or Formula XVI are generally commercially available or can be prepared by known procedures.

Suitable solvents for use in the above Process C are generally polar high-boiling solvents such as dimethylformamide (DMF); glyme; tetrahydrofuran (THF); and pyridine. The preferred solvent is pyridine.

Suitable bases for use in the above Process C include tertiary amines such as triethylamine; and pyridine. The preferred base is pyridine.

The above Processes A and B, Method 1, can be carried out at temperatures between about -20° C. and about 100° C. Preferably, these reactions are carried out between about -5° C. and about 50° C.

The above Process B, Method 2, can be carried out at temperatures between about -50° C. and about 150° C. Preferably when W is a halo radical, the reaction is carried out between about 0° C. and about 30° C. When W is alkoxy, the reaction is preferably carried out between about 100° C. and about 150° C. When W is methyl sulfonate, the reaction is preferably carried out between about -20° C. to about 20° C. When W is an ester, the reaction is preferably carried out between about 0° C. and about 50° C.

Process C can be carried out at temperatures between about 10° C. and 200° C. Preferably, this reaction is carried out between about 70° C. and about 100° C.

Process D can be carried out at temperatures between about 0° C. and 100° C. Preferably, these reactions are carried out between about 0° C. and about 50° C.

Preparation of the compounds of the present invention by processes A, B, C and D are preferably carried out at about atmospheric pressure, although higher or lower pressures can be used if desired.

Substantially equimolar amounts of reactants are preferably used in processes A, B and C, although higher or lower amounts can be used if desired.

Generally, about one equivalent of base is used per equivalent of starting material of Formula III, VI, XII and/or XIV. Where the acid addition salt of the mono-substituted hydrazine of Formula IV is used, one additional equivalent of base is used. For example, in Process A, when substituents A and B are the same and a monosubstituted hydrazine is used, about two equivalents of base are used since about two equivalents of a suitably substituted benzoyl chloride of Formula III or VI are employed. In Process A, when substituents A and B are different and an acid addition salt of the monosubstituted hydrazines of Formula IV is used, about two equivalents of base are used in Step 1 and about one equivalent of base is used in Step 2.

Modifications to the above processes may be necessary to accommodate reactive functionalities of particular A and/or B substituents. Such modifications would be apparent and known to those skilled in the art.

It will be appreciated by those skilled in the art that electronic forces may give rise to more than one isomer of the compounds of Formula II such as enantiomers, conformers and the like. There may be a difference in properties such as physical characteristics and degree of biological activity between such isomers. Separation of a specific isomer can be accomplished by standard techniques well known to those skilled in the art such as silica gel chromatography.

The agronomically acceptable salts embraced by Formula I of the invention can be prepared by reacting a metal hydroxide, a metal hydride or an amine or ammonium salt, such as a halide, hydroxide or alkoxide with a compound of Formula I having one or more hydroxy or carboxy groups or reacting a quaternary ammonium salt, such as chloride, bromide, nitrate or the like with a metal salt of a compound of Formula I in a suitable solvent. When metal hydroxides are used as reagents, useful solvents include water; ethers such as glyme and the like; dioxane; tetrahydrofuran; alcohols such as methanol, ethanol, isopropanol and the like. When metal hydrides are used as reagents, useful solvents include nonhydroxylic solvents, for example, ethers such as dioxane, glyme, diethylether and the like; tetrahydrofuran; hydrocarbons such as toluene, xylene, hexane, pentane, heptane, octane and the like; dimethylformamide, and the like. When amines are used as reagents, useful solvents include alcohols, such as methanol or ethanol; hydrocarbons, such as toluene, xylene, hexane and the like; tetrahydrofuran; glyme; dioxane; or water. When ammonium salts are used as reagents, useful solvents include water; alcohols, such as methanol or ethanol; glyme; tetrahydrofuran; or the like. When the ammonium salt is other than a hydroxide or alkoxide, an additional base, such as potassium or sodium hydroxide, hydride, or alkoxide is generally used. The particular choice of solvent will depend on the relative solubilities of the starting materials and the resultant salts, and slurries rather than solutions of certain reagents may be used to obtain the salts. Generally, equivalent amounts of the starting reagents are used and the salt-forming reaction is carried out at about 0° C. to about 100° C., preferably at about room temperature.

The acid addition salts of the present invention can be prepared by reacting hydrochloric, hydrobromic, sulfuric, nitric, phosphoric, acetic, propionic, benzoic or other suitable acid with a compound of Formula I having a basic functional group in a suitable solvent. Useful solvents include water, alcohols, ethers, esters, ketones, haloalkanes and the like. The particular choice of solvent will depend on the relative solubilities of the starting materials and the resulting salts and slurries rather than solutions of certain reagents may be used to obtain the salts. Generally, equivalent molar amounts of starting materials are used and the salt-forming reaction is carried out at from about -10° C. to about 100° C., preferably at about room temperature.

The following examples will further illustrate this invention but are not intended to limit it in any way. In Table I, some N'-substituted-N,N'-disubstitutedhydrazines of the present invention that have been made are listed. The structure of these compounds was confirmed by NMR and in some cases by IR and/or elemental analysis. Specific illustrative preparation of the compounds of Examples 1, 3, 16, 44, 102, 103, 148, 220, 295, 324, 625, 635, 636, 637, 638, 639, 642, 646, 648, 654, 656, 659, 660, 682, 683, 688, 689, 691, 699, 702, 722, 723, 724, 727, 729, 733, 737, 738, 739, 743, 754, 755, 764, 765, 766, 767, 772, 778, 787, 802, 809, 822, 829, 837, 853, 855, 864, 870 to 873, 878, 880, 882, 883, 893, 905, 914, 918, 922, 923, 933, 941, 942, 944, 948, 1002, 1008, 1013 and 1015 to 1018 are described after Table I.

    TABLE I       ##STR20##        where G.sub.2 N is a single bond when R.sup.2 is "H" and is a double      bond when R.sup.2 is "" Ex. No. G.sub.2 (X) G.sub.2 (X') R.sup.1 R.sup.2 A       B         1 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.4      Cl-4  2 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-3 C.sub.6      H.sub.4 Cl-3  3 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.5  4 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.3 Cl.sub.2 -3,4      C.sub.6 H.sub.3 Cl.sub.2 -3,4  5 C(O) C(O) C(CH.sub.3).sub.3 H  C.sub.6      H.sub.4 CH.sub.3 -4 C.sub.6 H.sub.4 CH.sub.3 -4       6 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 NO.sub.2 -4 C.sub.6      H.sub.4 NO.sub.2 -4  7 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4      OCH.sub.3 -4 C.sub.6 H.sub.4 OCH.sub.3 -4  8 C(O) C(O) C(CH.sub.3).sub.3      H C.sub.6 H.sub.4 NO.sub.2 -3 C.sub.6 H.sub.4 NO.sub.2 -3  9 C(O) C(O)      C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 OCH.sub.3 -3 C.sub.6 H.sub.4      OCH.sub.3 -3  10 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 NO.sub.2      -2 C.sub.6 H.sub.4 NO.sub.2 -2  11 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.4 Cl-2 C.sub.6 H.sub.4 Cl-2  12 C(O) C(O) C(CH.sub.3).sub.3 H      C.sub.6 H.sub.4 OCH.sub.3 -2 C.sub.6 H.sub.4 OCH.sub.3 -2  13 C(O) C(O)      C(CH.sub.3 ).sub.3 H C.sub.6 H.sub.4 CH.sub.3 -4 C.sub.6 H.sub.5  14      C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CN-4 C.sub.6 H.sub.4 CN-4      15 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH.sub.3 -4 C.sub.6      H.sub.4 Cl-4  16 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.4 Cl-4  17 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.4 Cl-3  18 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.4 Cl-2  19 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH.sub.3      -3 C.sub.6 H.sub.4 CH.sub.3 -3  20 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.4 CH.sub.3 -2 C.sub.6 H.sub.4 CH.sub.3 -2       21 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4      CH.sub.3 -4  22 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.4 CH.sub.3 -3  23 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5      C.sub.6 H.sub.4 CH.sub.3 -2  24 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.4 OCH.sub.3 -4  25 C(O) C(O) C(CH.sub.3).sub.3 H      C.sub.6 H.sub.5 C.sub.6 H.sub.4 OCH.sub.3 -3       26 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4      OCH.sub.3 -2  27 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.4 C(CH.sub.3).sub.3 -4  28 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.4 CN-4  29 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.4 NO.sub.2 -4  30 C(O) C(O) C(CH.sub.3).sub.3 H      C.sub.6 H.sub.5  C.sub.6 H.sub.4 NO.sub.2 -3       31 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4      NO.sub.2 -2  32 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4       C(CH.sub.3).sub.3 -4 C.sub.6 H.sub.4 C(CH.sub.3).sub.3 -4  33 C(O) C(O) C      (CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH.sub.3 -4 C.sub.6 H.sub.3 Cl.sub.2      -3,4  34 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4      F-4  35 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4      F-3  36 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4      F-2  37 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.3 Cl.sub.2 -3,5      C.sub.6 H.sub.3 Cl.sub.2 -3,5  38 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.3 Cl.sub.2 -2,4  39 C(O) C(O) CH(CH.sub.3).sub.2 H C      .sub.6 H.sub.5 C.sub.6 H.sub.5  40 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.4 CF.sub.3 -4  41 C(O) C(O) C(CH.sub.3).sub.3 H      C.sub.6 H.sub.5 C.sub.6 H.sub.4 CF.sub.3 -3       42 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4      CF.sub.3 -2  43 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.3 F.sub.2 -2,5  44 C(O) C(O) CH.sub.2 C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.5  45 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.4 CN-3  46 C(O) C(O) CH(CH.sub.3)CH.sub.2 CH.sub.3      H C.sub.6 H.sub.5 C.sub.6 H.sub.5  47 C(O) C(O) C(CH.sub.3).sub.3 H      C.sub.6 H.sub.5 C.sub.6 H.sub.3 F.sub.2 -2,6       48 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.5      49 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.3      Cl.sub.2 -3,4  50 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.3 Cl.sub.2 -3,5  51 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5      C.sub.6 H.sub.3 Cl.sub.2 -2,6  52 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.4 C(CH.sub.3).sub.3 -4 C.sub.6 H.sub.5       53 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-2 C.sub.6 H.sub.5      54 C(O) C(O) C(CH.sub.3).sub.3 H       ##STR21##       C.sub.6 H.sub.5       55 C(O) C(O) C(CH.sub.3).sub.3 H      ##STR22##       ##STR23##         56 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-3 C.sub.6 H.sub.5       57 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.3      Cl.sub.2 -3,4  58 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-2      C.sub.6 H.sub.3 Cl.sub.2 -3,4  59 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.4 CH.sub.3 -2 C.sub.6 H.sub.5  60 C(O) C(O) C(CH.sub.3).sub.3 H      C.sub.6 H.sub.5 C.sub.6 H.sub.3 Cl-2-NO.sub.2 -4       61 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.3      (NO.sub.2).sub.2 -3,5  62 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5      C.sub.6 H.sub.3 Cl.sub.2 -2,3       63 C(O) C(O) CH(CH.sub.3)C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.5  64 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub. 6      H.sub.3 Cl-2-CH.sub.3 -5  65 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.3 (CH.sub.3).sub.2 -3,5       66 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.3      NO.sub.2 -2-CH.sub.3 -5  67 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.3 CH.sub.3 -2-Cl-3  68 C(O) C(O) C(CH.sub.3).sub.3      H C.sub.6 H.sub.5 C.sub.6 H.sub.3 Cl-3-CH.sub.3 -4  69 C(O) C(O)      C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.3 NO.sub.2 -2-Cl-3  70      C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.3 OCH.sub.3      -3-NO.sub.2 -4  71 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.3 NO.sub.2 -2-OCH.sub.3 -3  72 C(O) C(O) C(CH.sub.3).sub.3 H      C.sub.6 H.sub.5 C.sub.6 H.sub.3 (NO.sub.2).sub.2 -2,4  73 C(O) C(O)      C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.4 Cl-2  74 C(O)      C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.4 Cl-3  75      C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.4      CH.sub.3 -4  76 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4      C.sub.6 H.sub.3 Cl.sub.2 -3,5  77 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.4 Cl-4 C.sub.6 H.sub.3 Cl.sub.2 -2,4       78 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.4      CF.sub.3 -4  79 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.4 OSO.sub.2 CH.sub.3 -4  80 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.4 CH(CH.sub.3).sub.2 -4       81 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4      OCOCH.sub.3 -2  82 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.4 CH.sub.2 CH.sub.3 -4  83 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.4 Br-2  84 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.4 OH-4  85 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.4 CH.sub.3 -4 C.sub.6 H.sub.4 CH.sub.3 -2       86 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH.sub.3 -4 C.sub.6      H.sub.4 CH.sub.3 -2  87 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4      CH.sub.3 -4 C.sub.6 H.sub.3 Cl.sub.2 -2,4       88 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH.sub.3 -4 C.sub.6      H.sub.3 Cl.sub.2 -3,5  89 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4      CH.sub. 3 -4 C.sub.6 H.sub.4 Cl-2  90 C(O) C(O) C(CH.sub.3).sub.3 H      C.sub.6 H.sub.4 CH.sub.3 -4 C.sub.6 H.sub.4 F-4       91 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 CH.sub.3 -4 C.sub.6      H.sub.4 CF.sub.3 -4  92 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4      CH.sub.3 -4 C.sub.6 H.sub.4 Cl-3  93 C(O) C(O) C(CH.sub.3).sub.3 H      C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.4 CH.sub.2 Cl-3  94 C(O) C(O)      C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.4 CH.sub.2 Cl-4      95 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.4      CH.sub.3 -2  96 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4      C.sub.6 H.sub.4 OCH.sub.3 -3  97 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.4 Cl-4 C.sub.6 H.sub.4 CH.sub. 3 -3       98 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 F-4 C.sub.6 H.sub.4      F-4  99 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 F-3 C.sub.6      H.sub.4 F-3 100 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 F-2      C.sub.6 H.sub.4 F-2       101 C(O) C(O) C(CH.sub.3).sub.3 H      ##STR24##       ##STR25##        102 C(S) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.4 Cl-4 C.sub.6 H.sub.5      103 C(O) C(S) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.5 104      C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4 Br-4 105      C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4 Br-3 106      C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6 H.sub.4 CH.sub.2      CH.sub.2 CH.sub.2 CH.sub.3 -4 107 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6      H.sub.4 CH.sub.2 CH.sub.3 -4 C.sub.6       H.sub.5 108 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.3 Cl.sub.2 -3,4 C      .sub.6 H.sub.5 109 C(O) C(O) C(CH.sub.3).sub.3 H C.sub.6 H.sub.5 C.sub.6      H.sub.4 COCH.sub.3 -4 110 C(O) C(O) CH.sub.2 C(CH.sub.3).sub.3 H C.sub.6      H.sub.5 C.sub.6 H.sub.4      ##STR26##

EXAMPLE NO. 1 -Preparation of N'-t-butyl-N,N'-(4-chlorobenzoyl)hydrazine

A suspension of t-butylhydrazine hydrochloride (12.5 g, 0.1 mole) in toluene (100 ml) at 0°-5° C. was treated slowly with 1 equivalent of NaOH solution, prepared from diluting 8 g of 50% NaOH commercially available solution to 20 ml of the volume with H₂ O. At 0° to 5° C. with mechanical stirring, 2 equivalents of 4-chlorobenzoyl chloride (35.9 g, 0.2 mole) and 2 equivalents of NaOH (16 g of 50% NaOH diluted with H₂ O to 40 ml) were added dropwise separately and simultaneously from dropping funnels. The exothermic reaction was cooled down by an ice-water bath through the entire addition. After the addition was completed, the resulting suspension was stirred at room temperature (RT) for one hour. The white precipitate (p.p.t.) was collected by suction-filtration and washed with a small amount of toluene and 100 ml of H₂ O. The material was then air-dried, then crystallized from 95% aqueous CH₃ OH to afford 24.65 g of N'-t-butyl-N,N'-(4-chlorobenzoyl)hydrazine as needles: m.p. 246°-248° C.

Additional product can be obtained by concentrating the mother liquor of crystallization.

EXAMPLE NO. 3 Preparation of N'-t-buty-1-N,N'-dibenzoylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (1.24 g, 10 mmoles) in toluene (50 ml) at room temperature, was added dropwise a solution of 50% aqueous sodium hydroxide (0.8 g, 10 ml). After 15 minutes, the reaction mixture was cooled to 5° C. and solutions of benzoyl chloride (2.82 gm, 20 ml) in toluene (7 ml) and 50% aqueous sodium hydroxide (1.6 g) were added dropwise and simultaneously from separate addition funnels while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was diluted with ether and the product isolated by filtration. The product was washed with water and ether and dried. The product was recrystallized from ethermethanol to afford N'-t-butyl-N,N'-dibenzoylhydrazine as a white powder: m.p. 174°-176° C.

EXAMPLE NO. 16 Preparation of N'-t-butyl-N'-(4-chlorobenzoyl)-N-benzoylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (1.24 g, 10 mmoles) in toluene (30 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (0.8 g, 10 mmole). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (1.42 g, 10 mmoles) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (0.8 g, 10 mmole) were added dropwise simultaneously from separate addition funnels while maintaining the temperature at or below 10°. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was diluted with toluene washed with water. The organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent removed under vacuum to afford a yellow oil which slowly solidifies on standing. The product was recrystallized from ether-hexane to afford white crystals.

To a stirred solution of the monobenzoylated compound (1.92 g, 10 mmoles) in toluene (30 ml) at 5° C., were added dropwise simultaneously from separate addition funnels, solutions of p-chlorobenzoyl chloride (1.75 g, 10 mmoles) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.8 g) while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The mixture was then diluted with hexane and the precipitated product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from ether-methanol to afford N'-t-butyl-N'-(4-chlorobenzoyl)-N-benzoylhydrazine as a white powder: m.p. 201°-204° C.

EXAMPLE NO. 44 Preparation of N'-neopentyl-N,N'-dibenzoylhydrazine

A solution of benzoylhydrazine (1.36 g, 10 mmoles), 1,1,1-trimethylacetaldehyde (0.86 g, 10 mmoles), and acetic acid (catalytic amount) in methanol are stirred at room temperature until hydrazone formation is complete. The reaction mixture is brought to a pH of 4 and sodium cyanoborohydride (0.75 g, 12.5 mmoles) is added slowly portionwise (the reaction is connected to an aqueous sodium hydroxide trap). Upon compleiion, the reaction is diluted with excess aqueous sodium hydroxide and the methanol is removed under vacuum. The product is partitioned into methylene chloride and washed with aqueous base and water. The organic layer is separated and dried over anhydrous magnesium sulfate The magnesium sulfate is filtered, and the methylene chloride removed under vacuum to afford the product as a yellow oil which solidifies on standing. The crude 2-neopentyl-1-benzoylhydrazine is benzoylated directly.

To a stirred solution of the 2-neopentyl-1-benzoylhydrazine in toluene (40 ml) at 5° C., were added dropwise and simultaneously solutions of benzoyl chloride (1.4 g, 10 mmoles) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.8 g) while maintaining the temperature below 10° C. After the addition, the reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was diluted with hexane and the precipitated product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from methanol to afford N'-neopentyl-N,N'-dibenzoylhydrazine as a white powder: m.p. 237°-239° C.

EXAMPLE NO. 102 Preparation of N'-t-butyl-N'-benzoyl-N-4-chlorothiobenzoylhydrazine

A mixture of 4-chloro-methylthio-thiobenzoate (3.0 g, 0.015 mol) and t-butyl hydrazine hydrochloride (2.0 g, 0.016 mol) in 5 ml of pyridine was heated at 90° C. for 18 hours. The mixture was poured into 0.1N HCl/ether. The layers were separated and the organic extracts were washed with 3 portions of 0.1N HCl followed by saturated aqueous NaHCO. After the extracts were dried over anhydrous magnesium sulfate, the solvents were removed under vacuum to afford 1.9 g of a brown solid. Chromatography on silica gel using ether (25%)-methylene chloride (25%)-hexane as eluant afforded 0.8 g of a golden yellow solid. The solid was dissolved in 3 ml of methylene chloride and treated with pyridine (1 ml) and benzoyl chloride (0.6 ml). After 24 hours at 23° C., the reaction mixture was poured onto 0.1N HCl/ether. The organic layer was washed with saturated aqueous sodium bicarbonate and was dried over anhydrous magnesium sulfate. Evaporation of solvents gave a yellow oil which was chromatographed on silica gel using ether (25%)-methylene chloride (25%)-hexane as eluant to give 0.15 g of N'-t-butyl-N'-benzoyl-N-4-chlorothiobenzoylhydrazine as a yellow solid: m.p. 160°-162° C.

EXAMPLE NO. 103 Preparation of N'-t-butyl-N'-thiobenzoyl-N-benzoylhydrazine

A mixture of N'-t-butyl-N-benzoyl hydrazine (60% purity, 1.0 g, 0.0031 mol) and S-(thiobenzoyl)-thioglycolic acid (1.0 g, 0.0047 mol) in 3 ml of pyridine was heated at about 90° C. for 24 hours. The dark colored mixture was cooled and poured into 0.1N HCl/ether. The organic layer was washed with three 15 ml portions of 0.1N HCl followed by saturated aqueous sodium bicarbonate. The organic extracts were dried over anhydrous magnesium sulfate. Evaporation of the solvents afforded 0.5 g of a brown oil which was recrystallized from ether-hexane to yield 0.2 g of N'-t-butyl-N'-thiobenzoyl-N-benzoylhydrazine as a tan solid m.p. 169°-171° C.

EXAMPLE NO. 14 Preparation of N'-t-butyl-N-(2-hydroxymethylbenzoyl)-N'-benzoylhydrazine

t-Butylhydrazine (0.1 mol) in 75 ml ethanol was treated with 50% aqueous sodium hydroxide (0.11 mol). Phthalide (0.1 mol) was added and the mixture was refluxed for 5 days. After cooling, water was added and the crude product was isolated by

filtration. Filtration through silica gel afforded N'-t-butyl-N-(2-hydroxymethylbenzoyl)hydrazine (3.0 g). m.p. 116°-118° C.

0.7 g of N'-t-butyl-N-(2-hydroxymethylbenzoyl)-hydrazine and 1.1 g benzoyl chloride are combined in 10 ml of 5% NaOH and stirred at room temperature for 1.5 hours. The solids are filtered off, washed with water, then ether, to afford 0.6 g of white solid N'-t-butyl-N-(2-(benzoyloxymethyl)benzoyl)-N'-benzoylhydrazine. m.p. 190°-191° C.

EXAMPLE NO. 220 Preparation of N-(3-toluoyl)-N'-t-butyl-N'-benzoylhydrazine Step 1

To a stirred suspension of t-butylhydrazine (51 g) in a mixture of dioxane and water (2:1) (150 ml) was added sodium hydroxide (32 g of a 50% aqueous solution). After 10 min., the solution was cooled to 5° C. and di-t-butyldicarbonate (42 g) was added dropwise so as to maintain the reaction temperature below 10° C. The reaction mixture was warmed and stirred 2 hours at room temperature. The reaction mixture was filtered, washed with water and dried to afford N-t-butyloxycarbonyl-N'-t-butylhydrazine (74 g) as a white crystalline solid. m.p. 69°-71° C.

Step 2

To a stirred solution of N-t-butyloxycarbonyl-N'-t-butylhydrazine (61 g) in toluene (120 ml) was added benzoyl chloride (45 g) and sodium hydroxide (31 g of a 50% aqueous sodium hydroxide solution) dropwise and simultaneously. After stirring for 1 hour at room temperature, the solid N-t-butyloxycarbonyl-N'-t-butyl-N'-benzoylhydrazine was filtered, washed with water, hexane and dried to afford 52 g of product. m.p. 167°-170° C.

Step 3

The N-t-butoxycarbonyl-N'-t-butyl-N'-benzoylhydrazine (52 g, 0.18 mol) was stirred at room temperature in a methanolic hydrochloric acid solution for 4 days. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate. The whte precipitate was filtered, washed with water and dried in vacuo to give 30 g of N'-t-butyl-N'-benzoylhydrazine. m.p. 124°-125° C.

Step 4

To a stirred mixture of N'-t-butyl-N'-benzoylhydrazine (1.0 g) in 15 ml toluene and aqueous sodium hydroxide (0.5 g of 50% NaOH) was added 3-toluoylchloride (0.9 g). After stirring for 2 hours, the product was isolated by filtration to give N'-t-butyl-N-(3-toluoyl)-N'-benzoylhydrazine in good yield. m.p. 111°-114° C.

EXAMPLE NO. 295 Preparation of N'-(1,1-dimethylethyl)-N,N'-dibenzoylhydrazine

To a gently refluxing solution of ethyl magnesium bromide (150 ml of 1M solution) was added acetone azine (20 g) dissolved in diethyl ether (80 ml). The solution was refluxed for three days. Upon cooling, a saturated solution of ammonium chloride (75 ml) was added. The aqueous layer was separated and washed twice with diethyl ether (150 ml). The combined ether extracts were dried over anhydrous magnesium sulfate, filtered and the ether removed at reduced pressure. The product was distilled through a vigreux column at 3 torr and collected in a dry ice/acetone cooled receiving flask. The boiling point was 40°-50°. 15 g of product was collected.

Oxalic acid (17 g) was dissolved in a solution of ethanol:diethyl ether (1:1) (150 ml) and water (3.3 g) was added. To this acid solution was added the hydrazone (13 g) dissolved in diethyl ether (30 ml). The solution was stirred for 24 hours then filtered. The solid is washed once with diethyl ether. The filtrate was concentrated and combined with the solid to afford a 77% yield (16.3 g) of the hydrazine oxalate.

The 1,1-dimethylethylhydrazine oxalate (2 g) was dissolved in toluene and neutralized with 50% aqueous sodium hydroxide. To this solution was added benzoyl chloride (4.02 g) and sodium hydroxide (50% Aq. solution) (2.45 g) at 25° C. The reaction mixture was warmed to room temperature and stirred 3 hours. The mixture was diluted with hexane and filtered to afford the product as a white solid (0.5 g).

EXAMPLE NO. 324 Preparation of N'-t-butyl--N-(thiobenzoyl)-N'-(3-toluoyl)hydrazine

S-(thiobenzoyl)thioglycolic acid (3.0 g) was dissolved in 20 ml pyridine, treated with t-butyl hydrazine hydrochloride (excess, ca. 4 g) and then was heated at ca. 120° C. for 14 hours. Water (120 ml) was added and the mixture was extracted with ether. The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated to give crude N'-t-butyl-N-(thiobenzoyl)hydrazine as a viscous yellow oil.

N't-butyl-N-(thiobenzoyl)hydrazine (ca. 1 g), m-toluoyl chloride (approx. 0.7 g) and 50% aqueous sodium hydroxide (6 drops) were mixed in 1 ml water and 10 ml toluene at 23° C. After stirring for 3 hours, ether-hexane was added and the product was isolated by filtration (0.25 g). m.p. 165°-168° C.

EXAMPLE NO. 344 Preparation of N'-t-butyl-N-[3-(N N-dimethylcarbamoyl)benzoyl)-N'-benzoylhydrazine

N-(3-hydroxybenzoyl)-N'-t-butyl-N'-benzoylhydrazine (0.2 g) was stirred in tetrahydrofuran (15 ml) at 23° C. Solid potassium t-butoxide (0.1 g) was added and the solution went from clear colorless to cloudy yellow. After stirring 10 minutes at room temperature, N,N-dimethylcarbamoyl chloride was added dropwise (0.1 g). With the addition the solution turned colorless and a precipitate appeared. Saturated aqueous NaHC03 and ether were added, the layers separated and the organic dried over magnesium sulfate, filtered and rotavapped to afford an oily solid.

EXAMPLE NO. 625 Preparation of N'-t-butyl-N-(4-(4,4-dimethyloxazol-2-yl)benzoyl)-N'-(3-toluoyl)hydrazine

1.2 g of N'-t-butyl-N-(4-carbomethoxybenzoyl)-N'-(3-toluoyl)hydrazine was heated in 2 ml of 2-amino-2-methyl-1-propanol at 90°-100° C. for 5 hours. After cooling, the mixture was diluted with ether/methylene chloride and washed with 0.1N HCl. The organic layer was evaporated to afford 1.0 g of the corresponding amide.

The amide in 10 ml of chloroform was treated with 0.25 g of thionyl chloride and stirred at 23° C. for 1.5 hours. Saturated aqueous sodium bicarbonate was added and the layers separated. Evaporation of the organic layer afforded the product as a foam.

EXAMPLE NO. 635 Preparation of N-methyl-N'-t-butyl-N,N'-dibenzoylhydrazine

To a stirred solution of N'-t-butyl-N,N'-dibenzoylhydrazine (2.5 g, 0.008M) in dimethylformamide (DMF) (30 ml) at room temperature under nitrogen was added portionwise sodium hydride (60% oil dispersion) (0.4 g, 0.009M). The mixture was stirred at room temperature for 0.5 hours, and then methyl iodide (1.0 g, 0.008M) was added dropwise. The reaction mixture was allowed to stir for 1 hour. The mixture was then diluted with water (50 ml), neutralized with 10% HCl, and the product extracted into methylene chloride (50 ml). The methylene chloride layer was washed with water (5×20 ml), dried over anhydrous magnesium sulfate, and the methylene chloride removed under vacuum to afford N-methyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil.

EXAMPLE NO. 636 Preparation of N-benzyl-N'-t-butyl-N,N'-dibenzoylhydrazine

To a stirred solution of N'-t-butyl-N,N'-dibenzoylhydrazine (2 g, 0.006M) in DMF (25 ml) at room temperature under nitrogen was added portionwise sodium hydride (60% oil dispersion) (0.3 g, 0.007M). The mixture was stirred at room temperature for 0.5 hours, and then benzyl bromide (1.2 g, 0.007M) was added dropwise. The reaction mixture was warmed to 60° C. and allowed to stir for 2 hours. The mixture was then diluted with water (50 ml), neutralized with 10% HCl, and the product extracted into methylene chloride (50 ml). The methylene chloride layer was washed with water (5×20 ml), dried over anhydrous magnesium sulfate, and the methylene chloride removed under vacuum to afford N-benzyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil.

EXAMPLE NO. 637 Preparation of N-allyl-N'-t-butyl-N,N'-dibenzoylhydrazine

To a stirred solution of N'-t-butyl-N,N'-dibenzoylhydrazine (3 g, 0.011M) in DMF (30 ml) at room temperature under nitrogen was added portionwise sodium hydride (60% oil dispersion) (0.5 g, 0.012M). The mixture was stirred at room temperature for 0.5 hours, and then allyl iodide (1.8 g, 0.01M) was added dropwise. The reaction mixture was warmed to 60° C. and stirred for 2 hours. The mixture was then diluted with water (50 ml), neutralized with 10% HCl, and the product extracted into methylene chloride (50 ml). The methylene chloride layer was washed with water (5×20 ml), dried over anhydrous magnesium sulfate, and the methylene chloride removed under vacuum to afford N-allyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil.

EXAMPLE NO. 638 Preparation of N-methoxymethyl-N'-t-butyl-N-N'-dibenzoylhydrazine

N'-t-butyl-N,N'-dibenzoylhydrazine (2 g, 0.007M) was stirred at room temperature in a two phase system of toluene-50% sodium hydroxide with 100 mg of phase transfer catalyst (tetra-n-butylammonium hydrogen sulfate). Methoxymethyl chloride (1.2 g, 0.015M) was added dropwise and the mixture was stirred 3 hours. The layers were separated and the toluene layer was washed several times with water (until the water washes were neutral). The toluene solution was dried over anhydrous magnesium sulfate and the toluene removed under vacuum to afford N-methoxymethyl-N'-t-butyl-N,N'-dibenzoylhydrazine as a thick oil.

EXAMPLE NO. 639 Preparation of N-methylthiomethyl-N'-t-butyl-N,N'-dibenzoylhydrazine

To a stirred suspension of sodium hydride (a 50% oil dispersion washed 2 times with 20 ml pentane) (0.21 g, 0.0043M) in dry DMF (20 ml) under nitrogen at room temperature, was added N'-t-butyl-N,N'-dibenzoylhydrazine (1 g, 0.0034M) portionwise as a solid. The mixture was stirred at room temperature for 1/2 hour and methylthiomethylchloride (0.34 g, 0.0035M) was added dropwise. The resulting mixture was heated at 50° C. overnight, cooled, diluted with methylene chloride and washed repeatedly with water. The organic layer was dried over anhydrous magnesium sulfate and the methylene chloride removed under vacuum. The oily residue was chromatographed on silica gel using methylene chloride to afford N-methylthiomethyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil (60% yield).

EXAMPLE NO. 642 Preparation of N-(2-propynyl)-N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine

To a stirred suspension of N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine (1.5 g) in dimethylformamide (DMF) (20 ml) was added sodium hydride (200 mg of 60% oil dispersion) portionwise. After 15 min., propargyl bromide (0.6 g) was added to the reaction mixture dropwise and the reaction stirred for 1 hour. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with water (5×20 ml). The organic layer was then dried over magnesium sulfate and the solvent removed under vacuum to afford N-(2-propynyl)-N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine as a yellow amorphous solid. The product, N-(2-propynyl)-N'-t-butyl-N-benzoyl-N'-(3,5-dimethylbenzoyl)hydrazine, was purified by column chromatography on silica gel (solvent system:methylene chloride) to afford a 70% yield as a white solid.

EXAMPLE NO. 646 Preparation of N'-t-butyl-N-cyclohexyl-carbonyl-N'-benzoylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (2.0 g, 0.016M) in toluene (30 ml) was added 50% sodium hydroxide (1.3 g, 0.016M). After 15 minutes, the mixture was cooled to 5° C. and cyclohexanecarbonylchloride (2.4 g, 0.016M) and 50% sodium hydroxide (1.3 g, 0.016M) were added separately and simultaneously so as to maintain the reaction temperature below 10° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 hr. The mixture was diluted with hexane and the solid product isolated by filtration. This product (1.5 g, 0.008M) was dissolved in a stirred mixture of toluene (30 ml) and cooled on ice. To this mixture was added benzoylchloride (1.1 g, 0.008M) and 50% sodium hydroxide (0.6 g, 0.008M) simultaneously. After addition, the mixture was stirred for 1/2 hr., diluted with hexane and the solid product, N'-t-butyl-N-cyclohexylcarbonyl-N'-benzyylhydrazine, isolated by filtration.

EXAMPLE NO. 648 Preparation of N'-t-butyl-N-valeryl-N-benzoylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (24.8 g, 0.20 mole) in toluene (150 ml) at 5° C. was added one equivalent of NaOH, prepared by diluting 16 g of 50% aqueous (aq.) NaOH to 30 ml. After addition, valeryl chloride (24 g, 0.2 mole) and another one equivalent of NaOH solution (30 ml) were dropwise added separately and simultaneously. The reaction mixture was warmed to room temperature and stirred for 40 min. The two phase mixture was separated and the organic layer was washed with water and brine. The organic layer was dried over Na₂ SO₄ and concentrated under vacuum to give a colorless oil.

To a stirred solution of 1-t-butyl-2-valerylhydrazine (4 g, 0.023M) in toluene (40 ml) at 5° C. was added benzoyl chloride (3.4 g, 0.024M) and 50% aq. sodium hydroxide (0.98 g, 0.024M). After addition, the mixture was warmed to room temperature and stirred 2.5 hr. The mixture was diluted with ethyl acetate (50 ml) and washed with water (2×25 ml) and brine (1×25 ml). The organic layer was dried over magnesium sulfate and concentrated under vacuum to afford N'-t-butyl-N-valeryl-N'-benzoyl-hydrazine as a yellow oil.

EXAMPLE NO. 654 Preparation of N'-t-butyl-N-phenylacetyl-N'-benzoylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (2.0 g, 0.016M) in toluene (30 ml) was added 50% sodium hydroxide (1.3 g, 0.016M). After 15 minutes, the mixture was cooled to 5° C. and phenylacetyl chloride (2.4 g, 0.016M) and 50% sodium hydroxide (1.3 g, 0.016M) were added separately and simultaneously so as to maintain the reaction temperature below 10° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 hr. The mixture was diluted with hexane and the solid product isolated by filtration. This product (3.2 g, 0.015M) was water (100 ml) and the solids were air dried overnight. The solids were dissolved in 10% aq. hydrochloric acid (300 ml) and were washed with ethyl acetate (3×300 ml). The ethyl acetate washes were combined and extracted with 10% aq. hydrochloric acid (250 ml). The 10% aq. hydrochloric acid layers were combined and were neutralized with 50% aq. sodium hydroxide while being stirred. Stirring was continued for 1 hour at room temperature. The mixture was suction filtered and rinsed with water (100 ml) and the solids were air-dried yielding a white solid (m.p. 125°-126° C.).

To a stirred solution of 1-t-butyl-1-benzoylhydrazine (1 g, 0.005M) in toluene (40 ml) cooled to 5° C. was added 3-chloro-2,2-dimethylpropionylchloride (1.2 g, 0.007M) and 50% aq. sodium hydroxide (0.45 g, 0.0056M) so as to maintain the temperature below 10° C. The mixture was warmed to room temperature and stirred 1 hr. The mixture was diluted with hexane (40 ml) and water (10 ml). The white solid product N'-t-butyl-N-(betachloropivaloyl)-N'-benzoylhydrazine was isolated by suction filtration, washed with 50 ml hexane and 50 ml water and- dried.

EXAMPLE NO. 661 Preparation of N'-t-butyl-N-(1,2,2-trichlorovinyl)carbonyl-N'-benzoylhydrazine

To a stirred suspension of tert-butylhydrazine hydrochloride (200 g, 1.61 mole) in acetone (400 ml) was dropwise added triethylamine (200 g, 1.98 mole). After addition, the mixture was refluxed for 3 hours while periodically adding magnesium sulfate (100 g total). The mixture was cooled to room temperature and funnel filtered. The filtrate was was dropwise added triethylamine (200 g, 1.98 mole). After addition, the mixture was refluxed for 3 hours while periodically adding magnesium sulfate (100 g total). The mixture was cooled to room temperature and funnel filtered. The filtrate was dried over magnesium sulfate and concentrated under vacuum at 5° C. until a slurry formed. The mixture was diluted with ethyl acetate (100 ml) and was filtered. The filtrate was distilled yielding a yellow oil (b.p. 121°-127° C.).

Into a stirred suspension of 1-t-butyl-2-acetonehydrazone (43 g, 0.34 mole) in toluene (250 ml) at 5° C. was added 10% aq. sodium hydroxide (200 ml, 0.50 mole). After addition, benzoylchloride (70 g, 0.50 mole) was added dropwise to this mixture. Stirring was continued for 2 hours at 5° C. and 72 hours at room temperature. The mixture was diluted with ethyl acetate (300 ml) and washed with water (3 x 200 ml) and brine (200 ml). The organic layer was dried over magnesium sulfate and concentrated at 35° C. under vacuum to afford a yellow oil.

A mixture of 1-t-butyl-1-benzoyl-2-acetone hydrazone (90 g, approximately 60% pure,approximately 0.3 mole), ethanol (500 ml, 200 proof) and 10% aq. hydrochloric acid (500 ml) was stirred overnight at room temperature. The mixture was concentrated under vacuum to a thick slurry. The slurry was suction filtered with a water wash (400 ml). The solids were air-dried overnight.

The solids were dissolved in a water (200 ml) and methanol (100 ml) solution on a steam bath. The mixture stood at room temperature overnight. The mixture was suction filtered and rinsed with cold water (100 ml) and the solids were air dried overnight. The solids were dissolved in 10% aq. hydrochloric acid (300 ml) and were washed with ethyl acetate (3×300 ml). The ethyl acetate washes were combined and extracted with 10% aq. hydrochloric acid (250 ml). The 10% aq. hydrochloric acid layers were combined and were neutralized with 50% aq. sodium hydroxide while being stirred. Stirring was continued for 1 hour at room temperature. The mixture was suction filtered and rinsed with water (100 ml) and the solids were air-dried yielding a white solid (m.p. 125°-126° C.).

To a stirred solution of 1-t-butyl-1-benzoylhydrazine (1 g, 0.005M) in toluene (40 ml) cooled to 5° C. was added 3-chloro-2,2-dimethylpropionylchloride (1.2 g, 0.007M) and 50% aq. sodium hydroxide (0.45 g, 0.0056M) so as to maintain the temperature below 10° C. The mixture was warmed to room temperature and stirred 1 hr. The mixture was diluted with hexane (40 ml) and water (10-20 ml). The white solid product N'-t-butyl-N-(betachloropivaloyl)-N'-benzoylhydrazine was isolated by suction filtration, washed with 50 ml hexane and 50 ml water and dried.

EXAMPLE NO. 660 Preparation of N'-t-butyl-N-(1,2,2-trichlorovinyl)carbonyl-'-benzoylhydrazine

To a stirred suspension of tert-butylhydrazine hydrochloride (200 g, 1.61 mole) in acetone (400 ml) was dropwise added triethylamine (200 g, 1.98 mole). After addition, the mixture was refluxed for 3 hours while periodically adding magnesium sulfate (100 g total). The mixture was cooled to room temperature and funnel filtered. The filtrate was dried over magnesium sulfate and concentrated under vacuum at 5° C. until a slurry formed. The mixture was dilued with ethylacetate (100 ml) and was filtered The filtrate was distilled yielding a lightly yellow tinted oil (b.p. 121°-127° C.).

To a stirred suspension of 1-t-butyl-2-acetonehydrazone (43 g, 0.34 mole) in toluene (250 ml) at 5° C. was added 10% aq. sodium hydroxide (200 ml, 0.50 mole). After addition, benzoylchloride (70 g, 0.50 mole) was added dropwise to the mixture. Stirring was continued for 2 hours at 5° C. and 72 hours at room temperature. The mixture was diluted with ethyl acetate (300 ml) and washed with water (3×200 ml) and brine (200 ml). The organic layer was dried over magnesium sulfate and concentrated at 35° C. under vacuum yielding a yellow oil.

A mixture of 1-t-butyl-1-benzoyl-2-acetone hydrazone (90 g, approximately 60% pure,approximately 0.3 mole), ethanol (500 ml, 200 proof) and 10% aq. hydrochloric acid (500 ml) was stirred overnight at room temperature. The mixture was concentrated under vacuum to a thick slurry. The slurry was suction filtered and washed with water (400 ml). The solids were air-dried overnight.

The solids were dissolved in a water (200 ml) and methanol (100 ml) solution on a steam bath. The mixture stood at room temperature overnight. The mixture was suction filtered and rinsed with cold water (100 ml) and the solids were air dried overnight. The solids were dissolved in 10% aq. hydrochloric acid (300 ml) and were washed with ethyl acetate (3×300 ml). The ethyl acetate washes were combined and extracted with 10% aq. hydrochloric acid (250 ml). The 10% aq. hydrochloric acid layers were combined and were neutralized with 50% aq. sodium hydroxide while being stirred. Stirring was continued for 1 hour at room temperature. The mixture was suction filtered and rinsed with water (100 ml) and the solids were air-dried yielding a white solid (m.p. 125°-126° C.).

To a stirred solution of 1-t-butyl-1-benzoylhydrazine (1.5 g, 0.008M) in methylene chloride at 5° C. was added, simultaneously and separately, trichloroacryloylchloride (1.7 g, 0.009M) and triethylamine (0.9 g, 0.009M). After addition, the reaction was warmed to room temperature and stirred for 3 h. The flask's contents were diluted with 50 ml methylene chloride and washed with water (3×75 ml) and brine solution (1×75 ml). The organic layer was dried over magnesium sulfate and the solvent removed under vacuum to afford N'-t-butyl-N-(1,2,2-trichlorovinyl)carbonyl-N'-benzoylhydrazine as a white solid product.

EXAMPLE 682 Preparation of N'-t-butyl-N-benzoyl-N'-n-pentanecarbonylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (1 g, 0.008M) in toluene (30 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (0.64 g, 0.008M). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (1.12 g, 0.008M) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (0.64 g, 0.008M) were added dropwise simultaneously from separate addition funnels while maintaining the temperature at or below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction was diluted with hexane and the solid N'-t-butyl-N'-benzoylhydrazine was isolated by filtration.

To a stirred solution of the monobenzoylated compound (1.4 g, 0.0073M) in toluene (30 ml) at 5° C., were added dropwise simultaneously from separate addition funnels, solutions of hexanoyl chloride (1 g, 0.0073M) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.58 g, 0.0073M) while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The mixture was then diluted with hexane and the solid product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from ether-methanol to afford N'-t-butyl-N-benzoyl-N'-n-pentanecarbonylhydrazine as a white powder. m.p. 117°-118° C.

EXAMPLE 683 Preparation of N'-t-butyl--N-benzoyl-N'-cyclohexanecarbonylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (1 g, 0.008M) in toluene (30 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (0.64 g, 0.008M). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (1.12 g, 0.008M) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (0.64 g, 0.008M) were added dropwise and simultaneously from separate addition funnels while maintaining the temperature at or below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction was diluted with hexane and the solid N'-t-butyl-N-benzoylhydrazine was isolated by filtration.

To a stirred solution of the monobenzoylated compound (1.4 g, 0.0073M) in toluene (30 ml) at 5° C., were added dropwise and simultaneously from separate addition funnels, solutions of cyclohexanecarbonyl chloride (1.1 g, 0.0073M) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.58 g, 0.0073 M) while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The mixture was then diluted with hexane and the solid product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from ether-methanol to afford N'-t-butyl-N-benzoyl-N'-cyclohexanecarbonylhydrazine as a white powder. m.p. 202°-204° C.

EXAMPLE 688 Preparation of N'-t-butyl-N-benzoyl-N'-pivaloylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (2 g, 0.016M) in toluene (50 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (1.28 g, 0.016M). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (2.3 g, 0.017M) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (1.36 g, 0.017M) were added dropwise simultaneously from separate addition funnels while maintaining the temperature at or below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was diluted with hexane and the solid N'-t-butyl-N-benzoylhydrazine was isolated by filtration.

To a stirred solution of the monobenzoylated compound (2 g, 0.010M) in pyridine (15 ml) was added pivaloyl chloride (1.8 g, 0.015M) and a catalytic amount of 4-dimethylamino pyridine. The mixture was heated to 60° C. and stirred for approximately 1 hr., cooled and diluted with methylene chloride. The organic layer was washed with 10% HCl (3×25 ml) and water (50 ml), dried over magnesium sulfate and the solvent removed under vacuum. The solid product was recrystallized from methanol-ether to afford N'-t-butyl-N-benzoyl-N'-pivaloylhydrazine in 60% yield as a white-solid. m.p. 217°-220° C.

EXAMPLE 689 Preparation of N'-t-buty-1-N-benzoyl-N'-phenylacetylhydrazine

To a stirred suspension of t-butylhydrazine hydrochloride (1 g, 0.008M) in toluene (30 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (0.64 g, 0.008M). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (1.12 g, 0.008M) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (0.64 g, 0.008M) were added dropwise simultaneously from separate addition funnels while maintaining the temperature at or below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction was diluted with hexane and the solid N'-t-butyl-N-benzoylhydrazine was isolated by filtration.

To a stirred solution of the monobenzoylated compound (1.5 g, 0.0078M) in toluene (30 ml) at 5° C., were added dropwise and simultaneously from separate addition funnels, solutions of phenylacetyl chloride (1.2 g, 0.008M) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.63 g, 0.0078M) while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The mixture was then diluted with hexane and the solid product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from ether-methanol to afford N'-t-butyl-N-benzoyl-N'-phenylacetylhydrazine as a white powder. m.p. 167°-169° C.

EXAMPLE 691 Preparation of N'-t-butyl-N-benzoyl-N'-(beta-trifluoromethylcrotonyl)hydrazine

N'-t-butyl-N-benzoylhydrazine (1.0 g,) in 2 ml toluene was added dropwise to a solution of beta-trifluoromethylcrotonyl chloride (prepared by addition of oxalyl chloride (1.3 g) to a solution of 1.5 g beta-trifluoromethylcrotonic acid in 5 ml toluene at 23° C.). After 30 min. at 23° C., the reaction mixture was partitioned between saturated aqueous sodium bicarbonate (20 ml) and ether (20 ml). The ether layer was evaporated under reduced pressure to about 10 ml and the excess hydrazine was removed by filtration. The filtrate was evaporated to give N'-t-butyl-N-benzoyl-N'-(beta-trifluoromethylcrotonyl)hydrazine as a colorless oil.

EXAMPLE 699 Preparation of N'-t-butyl-N-benzoyl-N'-methacryloylhydrazine

N'-t-butyl-N-benzoylhdyrazine (0.9 g) suspended in 10 ml toluene and 1 ml H20 containing 0.3 g 50% sodium hydroxide was treated with 1.2 g of methacryloyl chloride at 23° C. After 18 hours, 5 ml of hexane was added and N'-t-butyl-N-benzoyl-N'-methacryloylhydrazine was collected by filtration. m.p. 148°-152° C.

EXAMPLE 702 Preparation of N'-t-butyl-N'-cyclobutanecarbonyl-N-(4-chlorobenzoyl)hydrazine

To a stirred solution of N'-t-butyl-N-(4-chlorobenzoyl)hydrazine (2.0 9, 8.8 mmole) in toluene (35 ml) at 5° C. was added cyclobutanecarboxylic acid chloride (1.25 g, 10.5 mmole) in one portion. To the above mixture was dropwise added 50% NaOH solution (0.85 g, 10.6 mmole). After addition, the ice water bath was removed and the reaction mixture was stirred at room temperature overnight.

The mixture was diluted with hexane (30 ml) and H20 (30 ml) and stirred for another 30 min. The solid product was collected by suction-filtration and washed with H20 (100 ml) and hexane (100 ml) to yield 1.5 g of N'-t-butyl-N'-cyclobutanecarbonyl-N-(4-chlorobenzoyl)hydrazine.

EXAMPLE 722 Preparation of N'-t-buyl-N-benzoyl-N'-isonicotinoylhydrazine

N'-t-butyl-N-benzoylhydrazine (1.0 g, 0.0052 mol) was suspended in 20 ml of toluene. Isonicotinoyl chloride hydrochloride (0.93 g, 0.0052 mol) was added and then a solution of sodium hydroxide (1.25 g of 50% aqueous NaOH) in 5 ml of water was added dropwise. After stirring at 23° C. for 2 hours, the solids were removed by filtration, washed with water and dried in air. The crude product was chromatographed on silica gel using 5% methanol/methylene chloride as eluant to afford pure N'-t-butyl-N-benzoyl-N'-isonicotinoylhydrazine. m.p. >210° C.

EXAMPLE 723 Preparation of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-benzoylhydrazine

A solution of N'-t-butyl-N-(2-pyridinecarbonyl)hydrazine (1.0 g, 0.00518 mol) in 20 ml of toluene at 23° C. was treated sequentially with 50% sodium hydroxide (1.3 g) and benzoyl chloride (0.728 g). The mixture was stirred overnight. The solids were removed by filtration and washed with water to afford N'-t-butyl-N-(2-pyridinecarbonyl)-N'-benzoylh-ydrazine.

EXAMPLE 724 Preparation of N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine

A solution of N'-t-butyl-N-benzoylhydrazine (2.0 g) and nicotinoyl chloride hydrochloride in 20 ml of methylene chloride at 23° C. was treated dropwise with triethylamine (4 ml). The reaction mixture was stirred at 23° C. for 0.5 hours. Solids were removed by filtration. The filtrate was diluted with 10N HCl and ether. The layers were separated and the organic layer was washed with 10N HCl. The aqueous layer was neutralized with solid sodium bcarbonate and extracted with ether. The ether extracts were treated with charcoal and then dried with magnesium sulfate. Evaporation of solvents afforded a yellow oil which was chromatographed on silica gel using as eluant a mixture of 10% CH₃ OH, 40% CH₂ Cl₂, 50% Et₂ O to afford N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine as a yellow foam. m.p. 60°-63° C.

EXAMPLE 727 Preparation of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(2-nitrobenzoyl)hydrazine

A solution of N'-t-butyl-N-(2-pyridinecarbonyl)hydrazine (1.0 g, 0.00518 mol) in 20 ml of toluene was treated dropwise simultaneously with a solution of sodium hydroxide (1.24 g of 50% aqueous solution) in 5 ml of water and 2-nitrobenzoyl chloride (0.96 g). The resulting mixture was stirred at 23° C. overnight. Water was added and the mixture was extracted with ether. A second extraction was performed with methylene chloride and the combined organic extracts were dried over magnesium sulfate. Evaporation afforded 0.4 g of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(2-nitrobenzoyl)hydrazine as a yellow solid. m.p. 137°-140° C.

EXAMPLE 729 Preparation of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(2-bromobenzoyl)hydrazine

An aqueous solution of sodium hydroxide (1.24 g of 50% NaOH diluted with 5 ml of water) was added to a solution of N'-t-butyl-N-(2-pyridinecarbonyl)hydrazine (1.0 g, 0.00518 mol) in 20 ml of toluene at 23° C. The mixture was cooled and treated with 2-bromobenzoyl chloride (1.137 g, 0.00518 mol). The mixture was then stirred at 23° C. overnight. The solids were removed by filtration, washed with water and dried to afford 0.96 g of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(2-bromobenzoyl)hydrazine as a white solid. m.p. 179°-180° C.

EXAMPLE 733 Preparation of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(3,4-dichlorobenzoyl)hydrazine

A solution of N'-t-butyl-N-(2-pyridinecarbonyl)hydrazine (0.5 g) in 10 ml of toluene was treated with 50% sodium hydroxide (0.61 g). 3,4-dichlorobenzoyl chloride (0.6 g) was added and the mixture was stirred rapidly for 4 hours at 23° C. and then was allowed to stand for 48 hours. The solids were removed by filtration and washed with water to afford 0.75 g of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(3,4-dichlorobenzoyl)hydrazine as a white solid. m.p. 175°-178° C.

EXAMPLE 737 Preparation of N'-t-butyl-N-(5-bromonicotinoyl-N'-(4-chlorobenzoyl)hydrazine

N'-t-butyl-N'-(4-chlorobenzoyl)hydrazine was prepared substantially according to the procedure for preparing N'-t-butyl-N'-benzoylhydrazine described for Example 220 step 3 except 4-chlorobenzoyl chloride was used in place of benzoyl chloride.

A solution of N'-t-butyl-N'-(4-chlorobenzoyl)hydrazine (0.5 g, 0.0022 mol) and 5-bromonicotinic acid (0.44 g, 0.0022 mol) in 10 ml of methylene chloride containing triethylamine (0.33 g) was added to a solution of methanesulfonyl chloride (0.25 g, 0.0022 mol) in 10 ml of methylene chloride at 0° C. The resulting mixture was stirred at 23° C. for 2 hours and then was allowed to stand overnight at 23° C. Aqueous sodium bicarbonate was added and the layers were separated. The aqueous layer was re-extracted with methylene chloride. The organic extracts were evaporated to give a yellow solid which was triturated with hexane/methylene chloride to afford N'-t-butyl-N-(5-bromonicotinoyl)-N'-(4-chlorobenzoyl)hydrazine as an off-white solid. m.p. 193°-197° C.

EXAMPLE 738 Preparation of N'-t-butyl-N-(pyrazinecarbonyl)-N'-benzoylhydrazine

To a mechanically stirred solution of t-butylhydrazine hydrochloride (51 g, 0.41 mol) in dioxane (100 ml) and water (50 ml), cooled in an ice bath was treated with 50% sodium hydroxide (32 g). The resulting mixture was treated dropwise with di-t-butyl-dicarbonate (92 g, 0.42 mol) over about one-half of an hour. After complete addition, the reaction mixture was warmed to room temperature and stirred for 2 hours. The resulting white solid was filtered off, washed with water and air-dried to afford 74 g of N'-t-butyl-N-t-butoxycarbonylhydrazine, mp. 69°-71° C.

A mechanically stirred solution of N'-t-butyl-N-t-butoxycarbonylhydrazine (61 g, 0.32 mol) in toluene (120 ml) cooled in an ice bath, was treated dropwise and simultaneously with 50% sodium hydroxide (31 g) in water (50 ml) and benzoyl chloride (45 g). The addition was complete in 20 minutes and the resulting mixture was warmed to room temperature and allowed to stir for one hour. The resulting white solid was filtered, washed with water and air dried to afford 94 g of N-t-butoxycarbonyl-N'-benzoyl-N'-t-butylhydrazine, mp. 167°-170° C.

To a mechanically stirred solution of N-t-butoxycarbonyl-N'-benzoyl-N'-t-butylhydrazine (52 g, 0.18 mol) in methanol (100 ml) was added concentrated hydrochloric acid (35 ml). The resulting mixture was stirred at room temperature for 4 days and then neutralized with saturated aqueous sodium bicarbonate. The resulting white solid was filtered, washed with water and dried under vacuum to afford N'-t-butyl-N-benzoylhydrazine (39 g) mp. 124°-125° C. solution of N'-t-butyl-N'-benzoylhydrazine (0.86 g, 0.0031 mol) and pyrazine carboxylic acid (0.56 g, 0.0045 mol) in 10 ml of methylene chloride at 23° C. This mixture was added to a solution of methane-sulfonyl chloride (0.6 g, 0.0052 mol) in 10 ml of methylene chloride at 0° C. The mixture was stirred at 23° C. for 3 hours and then allowed to stand at 23° C. overnight. Aqueous sodium bicarbonate was added and evaporated to give crude product which was triturated th ether to afford N'-t-butyl-N-(pyrazinecarbonyl)-N'-benzoylhydrazine as a white solid. m.p. 181°-83° C.

EXAMPLE 739 Preparation of N'-t-butyl-N-isonicotinoyl-N'-benzoylhydrazine

A solution of N'-t-butyl-N'-benzoylhydrazine (0.5 g, 0.00026 mol) in 10 ml of toluene was treated with 50% sodium hydroxide (0.6 g) followed by isonicotinyl chloride hydrochloride (0.47 g, 0.0026 mol). The mixture was stirred at 23° C. overnight. The solids were removed by filtration and washed with isonicotinyl-N'-benzoylhydrazine.

EXAMPLE 743 Preparation of N'-t-butyl-N-(2-pyridinecarbonyl)-N'-(4-fluorobenzoyl)hydrazine)

By substantially following the procedures described above for Example 2, except using 4-fluorobutyl-N((2-pyridinecarbonyl)-N'-(4-fluorobenzoyl)-N'-t-hydrazine was afforded.

EXAMPLES 754 AND 755 Preparation of N'-t-butyl-N'-(2-pyridinecarbonyl)-N-benzoylhydrazine

To a suspension of 2-picolinic acid (12.8 g, 0.104 mol.) in methylene chloride (80 ml) were added dropwise triethylamine (14 g, 0.139 mol.) in 10 ml methylene chloride followed by methanesulfonyl chloride (13 g, 0.113 mol.) in 10 ml methylene chloride at 0° C. The resulting mixture was stirred for half an hour before the dropwise addition of N'-t-butyl-N-benzoylhydrazine (20.0 g, 0.10 mole) in 80 ml methylene chloride at 0° C. to 23° C. The final dark brown mixture was allowed to stir at 23° C. for one hour, and to stand at 23° C. overnight.

Aqueous sodium bicarbonate was added and the layers were separated. The aqueous layer was re-extracted with methylene chloride. The organic extracts were combined, and dried over magnesium sulfate. Evaporation under reduced pressure gave 25 g of a light green, brown solid. Recrystalization on a steam bath with ethyl acetate:hexane (80:20v/v) afforded a light yellow solid.

Column chromatography on silica gel, eluted first with methylene chloride and ether and then with ethyl acetate afforded two separate isomers of N'-t-butyl-N'-(2-pyridinecarbonyl)-N-benzoylhydrazine.

EXAMPLE 764 Preparation of N'-t-butyl-N-benzoyl-N'-(2-furoyl)hydrazine

N'-t-butyl-N-benzoylhydrazine (1 g) was dissolved in 20 ml toluene. Water (5 ml) and 50% aqueous sodium hydroxide (1.25 g) was added followed by 2-furoylchloride (0.68 g). After stirring for 7 hours at room temperature, 0.3 g 2-furoylchloride was added and the mixture stirred for a further 6 hours. The solid product, N'-t-butyl-N-benzoyl-N'-(2-furoyl)hydrazine, was removed by filtration and washed with water. m.p. 155°-175° C.

EXAMPLE 765 Preparation of N'-t-butyl-N-benzoyl-N'-(2-thiophenecarbonyl)hydrazine

N'-t-butyl-N-benzoylhydrazine (1.0 g) was dissolved in 20 ml toluene. 50% aqueous sodium hydroxide (1.25 g) was added followed by 2-thiophenecarbonylchloride (0.76 g). The mixture was stirred at room temperature for 14 hours. The solid product, N'-t-butyl-N-benzoyl-N'-(2thiophenecarbonyl)hydrazine, was removed by filtration and washed with water. m.p. >200° C.

EXAMPLE 766 Preparation of N'-t-butyl-N-(2-thiophenecarbonyl)-N'-benzoylhydrazine

N'-t-butyl-N-(2-thiophenecarbonyl)hydrazine (1 g) was dissolved in 10 ml toluene and treated with 50% aqueous sodium hydroxide (1.0 g) and water (2 ml) followed by benzoylchloride (0.8 g). After stirring for 14 hours at room temperature, the solid product, N'-t-butyl-N-(2-thiophenecarbonyl)-N'-benzoylhydrazine, was removed by filtration and washed with water. m.p. >190° C.

EXAMPLE 76 Preparation of N'-t-butyl-N-(2-furoyl)-N'-benzoylhydrazine

N'-t-butyl-N-(2-furoyl)hydrazine (1.0 g) was dissolved in 10 ml toluene and 2 ml water. 50% aqueous sodium hydroxide (1.0 g) was added followed by benzoylchloride (0.8 g). After stirring for 14 hours at room temperature, the solid product, N'-t-butyl-N-(2-furoyl)-N'-benzoylhydrazine, was removed by filtration and washed with water. m.p. 160°-162° C.

EXAMPLE 722 Preparation of N'-t-butyl-N-(4-methylbenzoyl)-N'-(2,5-dichlorothiophene-3-carbonyl)hydrazine

N'-t-butyl-N-4-methylbenzoylhydrazine (0.7 g) was dissolved in 35 ml toluene. Water (5 ml) and 50% aqueous sodium hydroxide (0.8 g) were added followed by 2,5-dichlorothiophene-3-carbonylchloride (2.0 g). After stirring for 3 hours at room temperature, ether was added and the organic layer separated. Evaporation afforded a solid which was triturated with 10% ether-hexane to afford N'-t-butyl-N-(4-methylbenzoyl)-N'-(2,5-dichlorothiophene-3carbonyl)hydrazine. m.p. 163°-165° C.

EXAMPLE 778 Preparation of N'-t-butyl-N-(N-methyl-2-pyrrolecarbonVI)-N'-benzoylhydrazine

N'-t-butyl-N-(N-methyl-2carbonylpyrrole)hydrazine (0.8 g) was dissolved in 10 ml toluene and 1 ml water. 50% aqueous sodium hydroxide (10 drops) was added followed by benzoylchloride (1.2 g). After 14 hours stirring at room temperature, ether was added and the product, N'-t-butyl-N-(N-methyl-2-pyrrolecarbonyl)-N'-benzoylhydrazine, was isolated by filtration and washed with ether. m.p. 182°-185° C.

EXAMPLE 787 Preparation of N'-t-butyl-N-(1,2,3-triazole-4-carbonyl)-N'-(3-methylbenzoyl)hydrazine

1,2,3-triazole-4-carboxylic acid (1.0 g) and triethylamine (0.9 g) were dissolved in 40 ml methylene chloride and cooled in an ice bath. Methanesulfonylchloride (1.0 g) was added dropwise. After addition was complete, the reaction mixture was stirred for 0.5 hours. N'-t-butyl-N'-(3methylbenzoyl)hydrazine (1.84 g) in 10 ml CH₂ Cl₂ was added dropwise. The resulting mixture was allowed to stand for 14 hours. Aqueous sodium bicarbonate was added. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to give a yellow oil. Chromatography on silica gel using acetone as eluant afforded N'-t-butyl-N-1,2,3-triazole-4-carbonyl-N'-(3-methylbenzoyl)hydrazine.

EXAMPLE NO. 802 Preparation of N'-(1-cyano-1-methyl)ethyl-N,N'-dibenzoylhydrazine

To a suspension of benzoylhydrazine (13.6 g, 0.1 mole) in deionized water (50 ml) at 5° C. with stirring was dropwise added concentrated hydrogen chloride (9.8 g, 0.1 mole). To the resulting clear solution was added sodium cyanide (5.2 g, 0.1 mole) and acetone (6.5 g, 0.11 mole). A white and thick precipitate appeared. The cooling bath was removed and the reaction flask was stoppered tightly. The reaction mixture was stirred for 18 hours. The precipitate was collected by suction-filtration and was washed with a small amount of water to give 17.5 g (86.2% yielded) of the desired intermediate, N'-(1-cyano-1-methyl)ethyl-N-benzoic acid hydrazide, as the starting material for the next step. (m.p. 82°-92° C.)

To the solution of N'-(1-cyano-1-methyl)ethyl-N-benzoic acid hydrazide (2 g, 0.01 mole) in dry methylene chloride (25 ml) under nitrogen at room temperature with stirring was added benzoyl chloride (2.02 g, 0.014 mole). To the above mixture was dropwise added triethylamine (1.31 g, 0.013 mole). The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with methylene chloride (50 ml), washed with water and brine. The organic layer was dried over MgSO₄ and the solvent was evaporated at reduced pressure to give a residue. The residue was treated with ethyl acetate/hexane mixture (1:1) affording a crude solid product which was collected by suction-filtration (1 g, 33% yield). An analytical sample was obtained by crystallization from ethyl acetate/hexane (4:1), m.p. 202°-204° C. NMR and IR spectra showed the desired product.

EXAMPLE NO. 809 Preparation of N'-(1-cyano-1-methyl)ethyl-N,N'-di-4-toluoylhydrazine

To the suspension of 4-toluic acid hydrazide (15.0 g, 0.1 mole) in water (150 ml) and ethanol (20 ml) at 5° C. with stirring was dropwise added concentrated hydrogen chloride (10 g, 0.1 mole). To the above suspension was carefully added sodium cyanide (5.3 g, 0.1 mole) and acetone (6.6 g, 0.11 mole). The reaction flask was stoppered tightly and the cooling bath was removed. The resulting viscous reaction mixture was stirred at room temperature for more than 24 hours. The precipitate was collected by suction-filtration and was washed with a small amount of diluted hydrogen chloride and water affording 14.6 g. (64.8%) of N'-(1-cyano-1-methyl)ethyl-4-toluic acid hydrazide as the starting material for the next step. Analytical sample was obtained by crystallization from ethyl acetate/hexane (3:1), m.p. 146°-148° C.

To the solution of N'-(1-cyano-1-methyl)ethyl-4-toluic acid hydrazide (2.17 g, 0.01 mole) in dry methylene chloride (65 ml) under nitrogen with magnetic stirring was added 4-dimethylaminopyridine catalyst (1.34 g, 0.011 mole) followed by 4-methylbenzoyl chloride (2.52 g, 0.017 mole). To the above mixture was dropwise added triethylamine (1.1 g, 0.011 mole). The reaction mixture was slightly exothermic. After stirring at room temperature for 40 minutes the reaction mixture was diluted with methylene chloride (50 ml), washed with diluted HCl solution (2×50 ml), dil NaOH (50 ml), H₂ O (50 ml) and brine. The organic layer was dried over MgS04, and the solvent was evaporated under reduced pressure to give a residue. The residue was treated with ethyl acetate/hexane mixture (1:1) and the resulting solid was collected by suction-filtration and affording 2.75 g (82% yield) of almost pure product. (m.p. 192°-198° C.) NMR and IR spectra showed the desired product.

EXAMPLE NO. 822 Preparation of N'-(1,1-dimethyl-3-butenyl)-N,N'-dibenzoylhydrazine

To a gently refluxing solution of allyl magnesium bromide (380 ml of lM solution) was added acetone azine (20 g) dissolved in diethyl ether (200 ml). The solution was refluxed for three days. Upon cooling, a saturated solution of ammonium chloride (50 ml) was added. The aqueous layer was separated and washed twice with diethyl ether (200 ml). The combined ether extracts were dried over anhydrous magnesium sulfate, filtered and the ether removed at reduced pressure. The product was distilled through a vigreux column at 3.1 torr and collected in a dry ice/acetone cooled receiving flask. The boiling point was 60°-65° C. 15 g of product was collected.

Oxalic acid (16.7 g) was dissolved in a solution of ethanol:diethyl ether (1:1) (150 ml) and water (3.3 g) was added. To this acid solution was added the hydrazone (13 g) dissolved in diethyl ether (75 ml). The solution was stirred for 24 hours then filtered. The solid is washed once with diethyl ether. The filtrate was concentrated and combined with the solid to afford a 71% yield (17.2 g) of the hydrazine oxalate.

The 1,1-dimethyl-3-butenylhydrazine oxalate (2 g) was dissolved in toluene and neutralized with 50% aqueous sodium hydroxide. To this solution was added benzoyl chloride (2.8 9) and sodium hydroxide (50% Aq. solution) (3.2 g) at 25° C. The reaction mixture was warmed to room temperature and stirred. The mixture was diluted with hexane and filtered to afford an oily product which solidified upon standing. (m.p. 105°-112° C.)

EXAMPLE NO. 829 Preparation of N'-t-butyl-N-benzoyl-N'-benzylhydrazine

Benzyl bromide (0.9 g), 1-benzoyl-2-t-butyl hydrazine (1 g) and triethylamine (0.52 g) were warmed in dimethylformamide (50 ml) at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with diethylether (100 ml) and washed three times with 25 ml of water. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed in vacuo to afford the product as a white solid. The product was chromatographed on silica gel (G:70 to 230 mesh) using methylene chloride as eluent to afford a 75% yield of a white solid: m.p. 147°-149.

EXAMPLE NO. 837 Preparation of N'-t-butyl-N-furoyl-N'-benzylhydrazine

Benzyl bromide (1.8 g), 1-furoyl-2-t-butyl hydrazine (2 g) and excess powdered potassium carbonate were stirred in dimethylformamide (50 ml) at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with diethyl ether and washed several times with water. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed in vacuo. The white solid product was chromatographed on silica gel (G:70°-230 mesh) using methylene chloride as eluent to afford the product in good yield: m.p. 152°-153.

EXAMPLE NO. 853 Preparation of N'-t-butyl-N-benzoyl-N'-methylpyridinylhydrazine

N'-t-butyl-N-benzoyl hydrazine (1.2 g), 2-chloromethyl pyridine (1.0 g) and triethylamine (2 equivalents) were stirred in dimethyl sulfoxide (15 ml) at room temperature for 2 hours. The reaction mixture was then warmed to 50° C. for 2 hours. The mixture was diluted with ether and washed with water. The organic layer was dried over magnesium sulfate, filtered and rotavapped to afford a yellow oil. The oil was chromatographed on silica gel (G:70°-230 mesh) using a methylene chloride-ether mixture (1:1) as eluent to afford the purified product as a yellow gum in approximately 20% yield.

EXAMPLE NO. 855 Preparation of N'-t-butyl--N-benzyl-N'-benzoylhydrazine

N'-t-butyl-N'-benzoyl benzaldehyde hydrazone (1.8 g) and sodium cyanoborohydride (1.5 equivalents) were stirred in dry methanol (30 ml) at room temperature. Ten percent HCl was added to bring the pH of the reaction mixture to pH 3°-4 and stirred at room temperature for 1 hour. The methanol was removed in vacuo and the residue was dissolved in methylene chloride. The methylene chloride layer was washed with saturated aqueous sodium bicarbonate and then with water. The organic layer was dried over magnesium sulfate, filtered and the solvent removed in vacuo to afford in good yield a white solid: m.p. 110°-115.

EXAMPLE NO. 864 Preparation of N'-t-butyl-N'-benzoylbenzaldehyde hydrazone

Benzaldehyde (10.6 g), t-butylhydrazine, hydrochloride (12.4 g) and triethylamine (10.1 g) were stirred in toluene (150 ml) at room temperature. The reaction mixture was washed with water and dried over magnesium sulfate. The mixture was filtered and the solvent was removed in vacuo to afford N'-t-butyl benzaldehyde hydrazone as a yellow oil in good yield.

The N'-t-butyl benzaldehyde hydrazone (1.76 g) and benzoyl chloride (1.4 g) were stirred in a pyridine-methylene chloride solvent system (1:1, 50 ml), diluted with methylene chloride and washed several times with 10% HCl. The organic layer was dried over magnesium sulfate, filtered and the solvent removed in vacuo to afford a low melting solid in good yield: m.p. 69°-72° C.

EXAMPLE NO. 870 Preparation of N-benzoyl-N'-t-buty-1-N'-phenylethylhydrazine

N'-t-butyl-N-benzoylhydrazine (2.2 g), powdered potassium carbonate (5 g) and beta-phenethyl bromide (1.8 g) were stirred in dimethylformamide (15 ml) at 60° for 18 hours. The reaction mixture was cooled, and diluted with ether and water. The white solid product was filtered off and recrystallized from ether/hexane to afford 0.3 g of product: m.p. 150°-152° C.

EXAMPLE NO. 871 Preparation of N-benzoyl-N'-t-butyl-N'-(ethoxycarbonyl)methylhydrazine

N'-t-butyl-N-benzoylhydrazine (2.0 g), powdered potassium carbonate (5 g) and bromoethyl acetate (1.6 g) were stirred in dimethylformamide (20 ml) at 60° C. for 14 hours. The reaction mixture was diluted with water and ether, and the organic layer was separated. The organic layer was washed several times with water, dried over magnesium sulfate and rotavaped to afford an oil. Chromatographic purification gave the pure oil product (0.25 g).

EXAMPLE NO. 872 Preparation of N'-t-butyl-N'-benzoyl-N-(4-tolyl)aminocarbonyl]hydrazine

N't-butyl-N'-benzoylhydrazine (0.8 g) and pmethylphenylisocyanate (0.9 g) were stirred in diethylether (10 ml) at 23° C. for 15 hours. The reaction mixture was diluted with ether and filtered to afford 0.5 g of solid product: m.p. 208°-210° C.

EXAMPLE 873 Preparation of N'-t-butyl-N'-benzoylcarbonyl-N-benzoylhydrazine

N'-t-butyl-N'-benzoylhydrazine (1 g), benzoyl formic acid (0.7 g) and methanesulfonyl chloride (0.7 g) were stirred in toluene (30 ml) and saturated sodium bicarbonate (10 ml) at approximately 5° C. Triethylamine was added slowly, dropwise to the reaction mixture and stirred 1 hour at room temperature. After stirring for 1 hour, the reaction mixture was diluted with toluene (25 ml) and washed with water several times. The organic layers were dried over magnesium sulfate, filtered and the toluene rotavapped off to afford a white solid. After column chromatography, the product was obtained as a white solid in approximately 70% yield.

EXAMPLE NO. 878 Preparation of N'-t-butyl-N-benzoylcarbonyl-N'-benzoylhydrazine

N'-t-butyl-N-benzoylhydrazine (1 g), benzoyl formic acid (1 g), and methanesulfonyl chloride (0.7 g) were stirred in toluene (35 ml) and saturated sodium bicarbonate (15 ml) at approximately 5° C. Triethylamine was added slowly, dropwise to the reaction mixture, and slowly warmed to room temperature. After stirring for 1 hour, the reaction mixture was diluted with toluene (20 ml) and the organic layer was washed several times with water. The organic layers were dried over magnesium sulfate, filtered and the toluene rotavapped off to afford a white gum. The crude product was chromatographed on silica gel (G:230-400 mesh) using a methylene chloride ether solvent system as eluent to afford a 65% yield of a white solid.

EXAMPLE NO. 880 Preparation of N'-t-butyl-N-(1,2,3,4-tetrahydronaphthyl-2-carbonyl)-N'-(3-toluoyl)hydrazine

To a stirred suspension of N'-t-butyl-N'-(3toluoyl)hydrazine (1.2 g) in toluene (10 ml) and aqueous sodium hydroxide (3 ml of 50% solution) was added 1,2,3,4-tetrahydronaphthyl-2-carbonyl chloride (0.007 mol). After stirring 1 hour, hexane and ether were added and the solids filtered off and dried by vacuum oven at 45° C.

EXAMPLE NO. 882 Preparation of N'-t-butyl-N-benzoyl-N'-(alpha-chlorophenylacetylhydrazine)

N'-t-butyl-N-benzoylhydrazine (10 g) was stirred in toluene (100 ml) and saturated sodium bicarbonate (50 ml) at approximately 5°-10° C. Alphachlorophenylacetylchloride (9.8 g) in toluene (20 ml) was added slowly, dropwise to the cooled reaction mixture, warmed to room temperature and stirred several hours Hexane (100 ml) was added to the reaction mixture and the solid product was filtered. The filter cake was washed several times with hexane and then water. The product was air dried to afford a 92% yield.

EXAMPLE NO. 883 Preparation of N'-t-butyl-N-benzoyl-N'-phenylacetylhydrazine

N'-t-butyl-N-benzoylhydrazine (2 g) was stirred in toluene (35 ml) and 50% aqueous sodium hydroxide (1 g) at 5° C. Phenylacetylchloride (1.5 g) was added slowly, dropwise to the reaction mixture, warmed to room temperature and stirred 1 hour. The reaction mixture was diluted with hexane (50 ml) and filtered off to yield a solid product. The filter cake was washed with hexane and water and allowed to air dry. The white solid product obtained in 90% yield melted at 167°-169° C.

EXAMPLE NO. 893 Preparation of N'-t-butyl-N'-benzoylalpha-furoyloxybenzaldehyde hydrazone

N'-benzoyl-N'-t-butyl hydrazine (1.5 g) was stirred in a two-phase solvent system consisting of toluene (20 ml) and 50% aqueous sodium hydroxide (10 ml). First, a phase transfer catalyst, (n-Bu)₄ N+-I (25-50 mg) was added and then 2-furoyl chloride was added dropwise. After the addition, the suspended white solid hydrazine went slowly into solution as it reacted to form the acylated product. After stirring at room temperature for 1 hour, the reaction mixture was diluted with 35 ml water and 30 ml of ethyl acetate. The layers were separated and the organic layer was washed several times with water, dried over magnesium sulfate, filtered and concentrated in vacuo to afford the product as a clear oil. The product was chromatographed on silica gel (G:230-400 mesh) using methylene chloride as the eluting solvent affording a clear, colorless oil (85% yield).

EXAMPLE NO. 905 Preparation of N'-t-butyl-N'-2,4-dichlorobenzoyl-alpha-methoxy-2,3-dimethylbenzaldehyde hydrazone

To a stirred solution of N'-t-butyl-N-(2,3-dimethylbenzoyl)hydrazine (4.2 g) and triphenylphosphine (5.5 g) in dry acetonitrile (60 ml) at room temperature under nitrogen was dropwise added carbon tetrachloride (3.5 g). The reaction mixture was stirred overnight at room temperature. The acetonitrile was removed in vacuo and the crude reaction mixture was chromatographed on silica gel (6, 230-400 mesh) using hexane/ethyl acetate (3:1) to afford the corresponding hydrazinoyl chloride as a yellow oil.

To a stirred suspension of powdered potassium carbonate (2 g) in methanol (75 ml) was added dropwise a solution of the above hydrazinoyl chloride (2.2 g) in methanol (40 ml). The reaction mixture was stirred overnight at room temperature, concentrated in vacuo and the carbonate was filtered off. The filtrate was rotavapped to afford methoxyhydrazine as a while solid (1.9 g).

To a stirred solution of the methoxyhydrazine (1.5 g) in toluene (25 ml) and 50% sodium hydroxide (2 g diluted with 8 g of water) was added 2,4-dichlorobenzoyl chloride (2.5 g) dropwise while the reaction mixture was kept at approximately 0° C. After warming to room temperature, the reaction mixture was diluted with ether and the layers separated. The organic layer was washed twice with water, once with saturated oodium chloride solution and dried over sodium sulfate. Concentration of the reaction gave a product which was chromatographed on silica gel (6, 230°-400 mesh) using a hexane/ethyl acetate (4:1) solvent system.

EXAMPLE NO. 914 Preparation of N'-t-butyl-N-benzenesulfonyl-N'-benzoylhydrazine

N'-t-butyl-N'-benzoylhydrazine (0.4 g) was stirred in pyridine (3 ml) at room temperature. Benzenesulfonyl chloride (0.5 g) was added slowly, dropwise and stirred for 2 hours, diluted with diethyl ether (20 ml) and washed several times with a 10% HCl solution and then water. The organic layer was dried over magnesium sulfate, filtered and the solvent rotavapped off to afford a white solid in good yield.

EXAMPLE NO. 918 Preparation of N'-t-butyl-N-benzoyl-N'-benzenesulfonylhydrazine

N-benzoyl-N'-t-butyl hydrazine (0.8 g) was stirred in pyridine (2 ml) at room temperature. Benzenesulfonyl chloride (0.8 g) was added slowly dropwise, stirred about 1 hour, diluted with diethyl ether (10 ml) and washed several times with a 10% HCl solution and then water. The organic layer was dried over magnesium sulfate. The mixture was filtered and the solvent rotavapped off to afford a white solid in good yield.

EXAMPLE NO. 922 Preparation of N'-t-butyl-N'-[methyl-(2-chlorophenylamino)phosphinyl]-N-benzoylhydrazine

Methyl dichlorophosphine (1.3 g) in ether (10 ml) and triethylamine (2 ml) were added to a stirred solution of N-benzoyl-N'-t-butyl hydrazine (1.0 g) in methylene chloride (3 ml). After stirring 5 minutes at room temperature, o-chloroaniline was added neat producing a mild exotherm. The reaction was quenched 2 minutes later with water (20 ml) and ether (20 ml), separated and the organic washed with 0.1N HCl, dried over MgSO₄, filtered and rotavapped to a colorless oil weighing 0.5 g.

EXAMPLE NO. 923 Preparation of N'-t-butyl-N-methylphenylphosphinyl-N'-benzoylhydrazine

Triethylamine (7 ml) and t-butyl hydrazine HCl (4 g) were stirred in methylene chloride (20 ml) at about 0° C. To this was added, slowly, methylphenylphosphinyl chloride (0.03 mol). The mixture was stirred at 0° C. for 15 minutes and quenched with a sodium bicarbonate solution. The reaction mixture was extracted with diethyl ether, washed with water and dried over magnesium sulfate. After filtering the drying agent, the solvent was removed in vacuo to afford an oily product which was used directly in the subsequent step.

N'-t-butyl-N-(methylphenyl)phosphinylhydrazine (0.7 g) and triethylamine (3 ml) were stirred in diethyl ether (30 ml) at room temperature. Slowly, dropwise benzoyl chloride (1.2 g) was added to the reaction mixture. After stirring 1 hour at room temperature, the reaction mixture was diluted with hexane and the solid product filtered off. The white solid melted at 175°-178° C.

EXAMPLE NO. 933 Preparation of N'-t-butyl-N-(2-phenyl-3-methylpentanoyl)-N'-(3-toluoyl)hydrazine

To a stirred suspension of N'-t-butyl-N'-(3toluoyl)hydrazine (0.7 g) in toluene (10 ml) and aqueous sodium hydroxide (12 drops of 50% aqueous sodium hydroxide) was added dropwise 2-phenyl-3-methyl-pentanoyl chloride (1.0 g). The reaction mixture was stirred overnight, diluted with hexanes and the solids filtered. The solids were washed with hexane and air dried.

EXAMPLE NO. 941 Preparation of N'-t-butyl-N-phenylpropiolyl-N'-(3-toluoyl)hydrazine

To a stirred solution of N'-(3-toluoyl)-N'-t-butyl hydrazine (1.0 g) in toluene (15 ml) and aqueous sodium hydroxide was added phenylpropiolyl chloride (0.01 mol) dropwise at room temperature. After stirring the reaction mixture for 3 hours, hexane and ether were added and the solids filtered. The solids were vacuum dried at 60° C.

EXAMPLE NO. 942 Preparation of N'-t-butyl-N-(2,3-di-methylbenzoyl)-N'-phenylpropiolylhydrazine

To a stirred solution of N-(2,3-dimethylbenzoyl)-N'-t-butyl hydrazine (1.0 g) in toluene (15 ml) and aqueous sodium hydroxide was added phenylpropiolyl chloride (0.006 mol) dropwise. After stirring 15 minutes at room temperature, ether and hexane were added and the solid product was filtered off.

EXAMPLE NO. 944 Preparation of N'-t-butyl-N-(3,4-epoxycyclohexane carbonyl)-N'-(3-toluoyl)hydrazine

To a stirred solution of N'-t-butyl-N'-(3toluoyl)hydrazine (20 g) in toluene (150 ml) and aqueous sodium hydroxide at 10° C. was added 3-cyclohexenecarbonyl chloride (14.3 g) dropwise at a rate which maintained the temperature at or below 10° C. After stirring at room temperature for 2 hours, hexane was added and the solids filtered. The filler cake was washed with hexane and water and dried overnight.

A mixture of N-(3-cyclohexenecarbonyl)-N'-t-butyl-N'-(3-toluoyl)hydrazine (2 g) and m-chloroperbenzoic acid (1.1 mol equivalents of 80% material) was stirred in methylene chloride (50 ml) overnight. The reaction mixture was diluted with methylene chloride (50 ml) and washed with saturated aqueous sodium bicarbonate solution (3×25 ml), dried over magnesium sulfate, filtered and rotavapped to afford the white solid epoxide in 78% overall yield.

EXAMPLE NO. 948 Preparation of N'-t-butyl-N-pyrenonecarbonyl-N'-(3-toluoyl)hydrazine

To a stirred suspension of t-butyl hydrazine hydrochloride (0.02 mol) in toluene (20 ml) and aqueous hydroxide (5 ml of 50% solution) at room temperature was added pyrenonecarbonyl chloride (0.01 mol). After stirring the reaction mixture for 20 minutes, ether and hexane were added and the solid product was filtered and washed with water. The solid product (0.5 g) was stirred in toluene (10 ml) and aqueous sodium hydroxide and m-toluoyl chloride (0.8 g) was added dropwise. After stirring for 5 hours, hexane and ether were added and the solid product filtered and air dried.

EXAMPLE NO. 1002 Preparation of 1-t-butyl-1-(3-toluoyl)-4-(4-chlorobenzenesulfonyl)semicarbazide

To a solution of N'-t-butyl-N'-3-toluoyl hydrazine (4.03 g, 0.02 mole) in methylene chloride (25 ml) under nitrogen was added 4-chlorobenzenesulfonyl isocyanate (5 g, 80%, 0.02 mole) at room temperature. The exothermic reaction mixture was stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure to give an oil. A precipitate appeared after treating with ether. The pure product was collected by suctionfiltration and washed with a small amount of ether affording 4.8 g of 1-t-butyl-1-(3-toluoyl)-4-(4-chlorobenesulfonyl)semicarbazide as a white solid. m.p 184°-188° C.

EXAMPLE NO. 1008 Preparation of N'-(1-methyl-1-carbamyl)ethyl-N-3-toluoyl-N-4-chlorobenzoyl hydrazine

To concentrated hydrochloric acid (10 ml) at 0° C. was added N'-(1-methyl-1-cyano)ethyl-N'-3-toluoyl-N-4-chlorobenzoyl hydrazine (0.8 g, 2.25 mmole) in one portion with stirring. After stirring for 40 minutes at a temperature below 20° C., the reaction mixture was diluted with water (50 ml) and hexane (50 ml). The resultant suspension was suction-filtered to give the product, N'-(1-methyl-1-carbamyl)ethyl-N'-3-toluoyl-N-4-chlorobenzoyl hydrazine, as a white solid. m.p. 213°-218° C. Yield is 0.5 g (59%).

EXAMPLE NO. 1013 Preparation of N'-t-butyl-N'-3-toluoylmucochloric acid hydrazone

To a solution of N'-t-butyl-N'-3-toluoylhydrazine (1.03 g, 5 mmole) in 80% methanol (25 ml) was added mucochloric acid (0.85 g, 5 mmole). The reaction mixture was held at room temperature for 2 hours with occasional shaking. The resultant viscous suspension was suction-filtered and washed with water. After air-drying overnight, the product, N'-t-butyl-3-toluoyl mucochloric acid hydrazone, weighed 1.50 g. m.p. 167°-168° C.

EXAMPLE NO. 1015 Preparation of N'-t-butyl-N'-3-toluoylethylpyruvate hydrazone

To a solution of N'-t-butyl-N'-3-toluoyl hydrazine (2.06 g, 10 mmole) in methylene chloride (20 ml) and water (20 ml) at room temperature with stirring was added ethylpyruvate (2.4 g, 21 mmole). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture turned to two phases. The aqueous phase was extracted with methylene chloride (2×50 ml) and the extracts were combined with the organic phase. The combined organic solution was washed with water and brine, dried over magnesium sulfate, filtered and evaporated to give a liquid product. The product was further dried in vacuum to give 1.9 g of N'-t-butyl-N'-3-toluoyl ethylpyruvate hydrazone as an oil.

EXAMPLE NO. 1016 Preparation of N'-t-butyl-N'-3-toluoylacetone hydrazone

To a solution of t-butyl acetone hydrazone (5 g, 39 mmole) in methylene chloride (50 ml) at 0° C. under nitrogen was added 3-toluoyl chloride (6.1 g, 39 mmole), followed by slowly adding triethylamine (3.94 g, 39 mmole). After the addition the reaction mixture was stirred at between 0°-5° C. for one hour. The reaction mixture was diluted with methylene chloride (100 ml) and washed subsequently with water, dilute HCl, water, and brine. The organic layer was dried over MgSO₄ and filtered. The solvent was evaporated under a reduced pressure to give a light brown liquid. The desired product, N'-t-butyl-N'-3-toluoyl acetone hydrazone, was obtained (2.45 g) by a vacuum distillation. b.p. 96°-104° C. at 0.05 mm Hg.

EXAMPLE NO. 1017 Preparation of N'-t-butyl-N'-3-toluoyl-N-isopropylhydrazine

To a solution of N'-t-butyl-N'-3-toluoyl acetone hydrazone (1.5 g, 6.08 mmole) in methanol (50 ml) at room temperature with stirring was added, in small portions, sodium borocyanohydride (0.5 g, 8 mmole). To the above reaction mixture was added 10% HCl (5 ml) and the mixture stirred for 10 minutes. A white precipitate appeared. To this was added water (50 ml) and dilute NaOH until the solution turned basic. The resultant white solid was collected by suction-filtration and washed with water. The product was further dried in vacuum to give 0.9 g (60%) of N'-t-butyl-N'-3-toluoyl-N-isopropylhydrazine as a fluffy white powder. m.p. 107°-109° C.

EXAMPLE NO. 1018 Preparation of N'-t-butyl-N'-benzoyl-N-(1-cyano-1-methyl)ethylhydrazine

To a suspension of N'-t-butyl-N'-benzoyl/hydrazine (1.92 g, 10 mmole) in water (30 ml) at 0°-5° C. was added concentrated HCl (1 g, 10 mmole), followed by NaCN (0.52 g, 10.6 mmole) and acetone (0.75 g, 12.9 mmole). After the addition, the reaction flask was stoppered tightly and the reaction mixture was stirred at room temperature for 16 hours. The resultant suspension was suction-filtered and washed with water. The product, N'-t-butyl-N'-benzoyl-N-(1-cyano-1-methyl)ethylhydrazine, was further dried in vacuum to give 2.1 g as a white powder. m.p. 117°-120° C.

By following substantially the procedures in Examples and 3 and using the reactants shown below in Table II the products of Example Nos. 2, 4 through 12, 14, 19, 20, 32, 37, 55, 98 through 101, 145, 169, 174, 181, 234, 250, 260, 264, 289, 295, 298, 308, 364, 390, 391, 394, 449, 613, 632, 924 through 928, 937, 938, 939, 943, 949, 950, 951, 954, 959, 961, 963, 964, 965, 967, 968, 990 and 996 were prepared.

                                      TABLE II                                     __________________________________________________________________________     Ex. No.                                                                             Compound of Formula III or VI                                                                  Compound of Formula IV                                                                      Base  Solvents                               __________________________________________________________________________      3   3-chlorobenzoyl  .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               4   3,4-dichlorobenzoyl                                                                             .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               5   4-methylbenzoyl  .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               6   4-nitrobenzoyl   .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               7   4-methoxybenzoyl                                                                                .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               8   3-nitrobenzoyl   .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               9   3-methoxybenzoyl                                                                                .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              10   2-nitrobenzoyl   .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               11  2-chlorobenzoyl  .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               12  2-methoxybenzoyl                                                                                .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               14  4-cyanobenzoyl   .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               19  3-methylbenzoyl  .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               20  2-methylbenzoyl  .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               32  4- .sub.- t-butylbenzoyl                                                                        .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               37  3,5-dichlorobenzoyl-                                                                            .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               55  1-naphthoylchloride                                                                             .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                                     hydrochloride                                                                               hydroxide                                                                            and water                               98  4-fluorobenzoyl  .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                               99  3-fluorobenzoyl  .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              100  2-fluorobenzoyl  .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              101  2-naphthoylchloride                                                                             .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                                     hydrochloride                                                                               hydroxide                                                                            and water                              145  4-biphenylbenzoyl                                                                               .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              169  2-chloromethyl-  .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     benzoyl chloride                                                                               hydrochloride                                                                               hydroxide                                                                            and water                              174  2-bromobenzoyl   .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              181  4-ethylbenzoyl   .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              234  3-methoxy benzoyl                                                                               .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              250  benzoyl chloride                                                                               2,2-dimethyl-                                                                               sodium                                                                               toluene                                                     pentylhydrazine                                                                             hydroxide                                                                            and water                                                   oxalic acid salt                                          260  2-nitro-4-chloro-                                                                               .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     benzoyl chloride                                                                               hydrochloride                                                                               hydroxide                                                                            and water                              264  2,6-difluorobenzoyl                                                                             .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              289  4-vinylbenzoyl   .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              295  benzoyl chloride                                                                               2,2-dimethyl-                                                                               sodium                                                                               toluene                                                     propylhydrazine                                                                             hydroxide                                                                            and water                                                   oxalic acid salt                                          298  2-bromobenzoyl  2,2-dimethyl-                                                                               sodium                                                                               toluene                                     chloride        propylhydrazine                                                                             hydroxide                                                                            and water                                                   oxalic acid salt                                          308  4-(1-propenyl)-  .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     benzoyl chloride                                                                               hydrochloride                                                                               hydroxide                                                                            and water                              364  4-bromobenzoyl   .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              390  3,5-dimethyl-    .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     benzoyl chloride                                                                               hydrochloride                                                                               hydroxide                                                                            and water                              391  2,4-dichlorobenzoyl                                                                             .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              394  2,3-dimethyl-    .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     benzoyl chloride                                                                               hydrochloride                                                                               hydroxide                                                                            and water                              449  3,4-dimethyl-    .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     benzoyl chloride                                                                               hydrochloride                                                                               hydroxide                                                                            and water                              613  2-acetoxybenzoyl                                                                                .sub.- t-butylhydrazine                                                                    NaHCO.sub.3                                                                          toluene                                     chloride        hydrochloride                                                                               i.e. sodium                                                                          and water                                                                bicarbonate                                  632  2-methyl-3-chloro-                                                                              .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     benzoyl chloride                                                                               hydrochloride                                                                               hydroxide                                                                            and water                              924  4-chlorobenzoyl methylhydrazine                                                                             sodium                                                                               toluene                                     chloride                     hydroxide                                                                            and water                              925  3,5-dichlorobenzoyl                                                                            methylhydrazine                                                                             sodium                                                                               toluene                                     chloride                     hydroxide                                                                            and water                              926   -n-pentanoylchloride                                                                           .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                                     hydrochloride                                                                               hydroxide                                                                            and water                              927   -n-heptanoyl    .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              928  chloroacetyl     .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              937  β,β-dimethyl                                                                          .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     acryloyl chloride                                                                              hydrochloride                                                                               hydroxide                                                                            and water                              938  2,3,3-trichloro-                                                                                .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     acryloyl chloride                                                                              hydrochloride                                                                               hydroxide                                                                            and water                              939  cinnamoyl        .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              943  cyclohexanecarbonyl                                                                             .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              949  2-furoylchloride                                                                                .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                                     hydrochloride                                                                               hydroxide                                                                            and water                              950  2-thiophene      .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     carboxylic acid hydrochloride                                                                               hydroxide                                                                            and water                                   chloride                                                                  951  pyrrolidine      .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     carbonylchloride                                                                               hydrochloride                                                                               hydroxide                                                                            and water                              954  N,N-diethylcarbamoyl                                                                            .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              959  benzoylchloride 2-tolyhydrazine                                                                             sodium                                                                               toluene                                                                  hydroxide                                                                            and water                              961  benzoylchloride phenylhydrazine                                                                             sodium                                                                               toluene                                                                  hydroxide                                                                            and water                              963  benzoylchloride 2-chloropphenyl                                                                             sodium                                                                               toluene                                                     hydroazine   hydroxide                                                                            and water                              964  benzoylchloride 4-chlorophenyl                                                                              sodium                                                                               touene                                                      hydrazine    hydroxide                                                                            and water                              965  benzoylchloride benzylhydrazine                                                                             sodium                                                                               toluene                                                                  hydroxide                                                                            and water                              967  3,5-dichlorobenzoyl                                                                            benzylhydrazine                                                                             sodium                                                                               toluene                                     chloride                     hydroxide                                                                            and water                              968  benzoylchloride 4-chloropyrazinyl                                                                           sodium                                                                               toluene                                                     hydrazine    hydroxide                                                                            and water                              990   -n-butanoyl     .sub.- t-butylhydrazine                                                                    sodium                                                                               toluene                                     chloride        hydrochloride                                                                               hydroxide                                                                            and water                              996  benzoyl         N'-(1,1-dimethyl)-                                                                          sodium                                                                               toluene                                     chloride        benzyl-N-benzoyl                                                                            hydroxide                                                                            and water                                                   hydrazine                                                 __________________________________________________________________________

By following substantially the procedures in Example 16 and using the reactants shown below in Table III, the products of Example Nos. 13, 15, 17, 18, 21 through 31, 33 through 36, 38, 40 through 43, 45, 47 through 54, 56, 57 through 62, 64 through 97, 104 through 109, 113, 117, 118, 119, 121, 122, 123, 125, 126, 130 through 135, 137 through 142, 146, 147, 150, 152 through 154, 160, 163, 167, 173, 175 through 180, 182, 183, 184, 190, 194 through 202, 204 through 211, 214 through 219, 224 through 231, 235 through 249, 251 through 259, 261 through 263, 265 through 270, 272 through 284, 287, 288, 290 through 292, 296, 297, 299 through 307, 309 through 322, 325, 327, 328, 334, 341 through 343, 346 through 348, 355 through 357, 370, 371, 377, 378, 380, 381, 387 through 389, 392, 393, 395, 396, 401 through 413, 419, 420, 422 through 424, 426 through 433, 437 through 448, 450 through 452, 454 through 457, 459 through 469, 474 through 483, 485 through 540, 542 through 545, 548 through 612, 615 through 624, 626 through 631, 633, 929 through 932, 934, 935, 936, 940, 946, 947, 952, 953, 962, 966, 993, 994, 995, 997 and 998 were prepared.

                                      TABLE III                                    __________________________________________________________________________     Example                                                                             Compound of                                                                              Compound of                                                                              Compound of                                           No.  Formula III                                                                              Formula VI                                                                               Formula IV                                                                              Base  Solvents                               __________________________________________________________________________      13  4-toluoyl chloride                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                                         hydrochloride                                                                           hydroxide                                                                            and water                               15  4-toluoyl chloride                                                                       4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               17  benzoylchloride                                                                          3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               18  benzoylchloride                                                                          2-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               21  benzoylchloride                                                                          4-methylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               22  benzoylchloride                                                                          3-methylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               23  benzoylchloride                                                                          2-methylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               24  benzoylchloride                                                                          4-methoxybenzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               25  benzoylchloride                                                                          3-methoxybenzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               26  benzoylchloride                                                                          2-methoxybenzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               27  benzoylchloride                                                                          4- .sub.- t-butylbenzoyl                                                                  .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               28  benzoylchloride                                                                          4-cyanobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               29  benzoylchloride                                                                          4-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               30  benzoylchloride                                                                          3-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               31  benzoylchloride                                                                          2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               33  4-methylbenzoyl                                                                          3,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               34  benzoylchloride                                                                          4-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               35  benzoylchloride                                                                          3-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               36  benzoylchloride                                                                          2-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               38  benzoylchloride                                                                          2,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               40  benzoylchloride                                                                          4-trifluoromethyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               41  benzoylchloride                                                                          3-trifluoromethyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               42  benzoylchloride                                                                          2-trifluoromethyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               43  benzoylchloride                                                                          2,5-difluorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               45  benzoylchloride                                                                          3-cyanobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               47  benzoylchloride                                                                          2,6-difluorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               48  4-chlorobenzoyl                                                                          benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                               49  benzoylchloride                                                                          3,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               50  benzoylchloride                                                                          3,5-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               51  benzoylchloride                                                                          2,6-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               52  4- .sub.- t-butylbenzoyl                                                                 benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                               53  2-chlorobenzoyl                                                                          benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                               54  1-naphthoylchloride                                                                      benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                                         hydrochloride                                                                           hydroxide                                                                            and water                               56  3-chlorobenzoyl                                                                          benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                               57  4-chlorobenzoyl                                                                          3,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               58  2-chlorobenzoyl                                                                          3,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               59  2-methylbenzoyl                                                                          benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                               60  benzoylchloride                                                                          2-chloro-4-nitro                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               61  benzoylchloride                                                                          3,5-dinitrobenzoyl                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               62  benzoylchloride                                                                          2,3-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               64  benzoylchloride                                                                          2-chloro-5-methyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               65  benzoylchloride                                                                          3,5-dimethylbenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               66  benzoylchloride                                                                          2-nitro-5-methyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               67  benzoylchloride                                                                          2-methyl-3-chloro                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               68  benzoylchloride                                                                          3-chloro-4-methyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               69  benzoylchloride                                                                          2-nitro-3-chloro                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               70  benzoylchloride                                                                          3-methoxy-4-nitro                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               71  benzoylchloride                                                                          2-nitro-3-methoxy                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               72  benzoylchloride                                                                          2,4-dinitrobenzoyl                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               73  4-chlorobenzoyl                                                                          2-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               74  4-chlorobenzoyl                                                                          3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               75  4-chlorobenzoyl                                                                          4-methylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               76  4-chlorobenzoyl                                                                          3,5-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               77  4-chlorobenzoyl                                                                          2,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               78  4-chlorobenzoyl                                                                          4-trifluoromethyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               79  benzoylchloride                                                                          4-methanesulfonyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               80  benzoylchloride                                                                          4-isopropylbenzoyl                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               81  benzoylchloride                                                                          2-acetoxybenzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               82  benzoylchloride                                                                          4-ethylbenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               83  benzoylchloride                                                                          2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               84  benzoylchloride                                                                          4-hydroxybenzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                               85  4-methylbenzoyl                                                                          2-methylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               86  4-methylbenzoyl                                                                          3-methylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               87  4-methylbenzoyl                                                                          2,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               88  4-methylbenzoyl                                                                          3,5-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               89  4-methylbenzoyl                                                                          2-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               90  4-methylbenzoyl                                                                          4-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               91  4-methylbenzoyl                                                                          4-trifluoromethyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               92  4-methylbenzoyl                                                                          3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               93  4-chlorobenzoyl                                                                          3-chloromethyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               94  4-chlorobenzoyl                                                                          4-chloromethyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                               95  4-chlorobenzoyl                                                                          2-methylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               96  4-chlorobenzoyl                                                                          3-methoxybenzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                               97  4-chlorobenzoyl                                                                          3-methylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              104  benzoylchloride                                                                          4-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              105  benzoylchloride                                                                          3-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              106  benzoylchloride                                                                          4- -n-butylbenzoyl                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              107  4-ethylbenzoyl                                                                           benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              108  3,4-dichloro-                                                                            benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              109  benzoylchloride                                                                          4-acetylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              113  benzoylchloride                                                                          2-iodobenzoyl                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              117  benzoylchloride                                                                          4-phenoxybenzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              118  4-trifluoromethyl-                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              119  4-trifluoromethyl-                                                                       3,4-dichlorobenoyl-                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              121  benzoylchloride                                                                          2-chloro-4-bromo-                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              122  benzoylchloride                                                                          4-phenylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              123  benzoylchloride                                                                          3,4,5-trimethoxy-                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              125  benzoylchloride                                                                          3-thiocyanomethyl-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              126  benzoylchloride                                                                          3-cyanomethyl-                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              130  4-ethylbenzoyl                                                                           3-toluoylchloride                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              131  4-ethylbenzoyl                                                                           4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              132  4-ethylbenzoyl                                                                           2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              133  benzoylchloride                                                                          3-ethylbenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              134  4-ethylbenzoyl                                                                           3-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              135  4-ethylbenzoyl                                                                           2-iodobenzoyl                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              137  benzoylchloride                                                                          4-carbomethoxy                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              138  2-bromobenzoyl                                                                           benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              139  2-trifluoromethyl-                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              140  benzoylchloride                                                                          3-iodobenzoyl                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              141  benzoylchloride                                                                          2-ethylbenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              142  benzoylchloride                                                                          3-methoxymethyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              146  benzoylchloride                                                                          2-nitro-4-(2-chloro-                                                                      .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               4-trifluoro-                                                                             hydrochloride                                                                           hydroxide                                                                            and water                                             methyl phenoxy)                                                                benzoylchloride                                                 147  2-nitro-4-(2-chloro-                                                                     benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     4-trifluoromethyl   hydrochloride                                                                           hydroxide                                                                            and water                                   phenoxy) benzoyl                                                               chloride                                                                  150  benzoylchloride                                                                          4-methylthio-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              152  benzoylchloride                                                                          3-bromo-4-methyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              153  benzoylchloride                                                                          3-methyl-4-bromo                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              154  benzoylchloride                                                                          2,4-dibromo                                                                               .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              160  benzoylchloride                                                                          3-phenoxy  .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              163  benzoylchloride                                                                          4-formyl benzoyl                                                                          .sub.-  t-butylhydrazine                                                               sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              167  benzoylchloride                                                                          2-acetoxybenzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              173  2-methyl-5-tri-                                                                          2-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     fluoromethyl        hydrochloride                                                                           hydroxide                                                                            and water                                   benzoylchloride                                                           175  4-ethylbenzoyl                                                                           3-ethyl    .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              176  benzoylchloride                                                                          4- -n-propyl                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              177  4-toluoyl chloride                                                                       3-bromo    .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              178  4-toluoyl chloride                                                                       3,5-dimethyl                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              179  benzoylchloride                                                                          4-iodobenzoyl                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              180  4-toluoyl chloride                                                                       4-ethyl benzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              182  4-toluoyl chloride                                                                       3-ethyl benzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              183  benzoylchloride                                                                          2-isopropylbenzoyl                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              184  3-ethyl benzoyl                                                                          benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              190  3-ethyl benzoyl                                                                          2,4-dichloro                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              194  4-methoxybenzoyl                                                                         3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              195  4-methoxybenzoyl                                                                         benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              196  2-chlorobenzoyl                                                                          3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              197  2-chlorobenzoyl                                                                          2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              198  2-chlorobenzoyl                                                                          4-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              199  2-chlorobenzoyl                                                                          4-ethyl benzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              200  4-ethyl benzoyl                                                                          3,5-dimethyl                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              201  4-ethyl benzoyl                                                                          2-chloro-4-methyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              202  benzoylchloride                                                                          3-acetoxybenzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              204  4-ethyl benzoyl                                                                          2-nitro-3-methyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              205  4-methoxybenzoyl                                                                         3,5-dimethyl                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              206  4-methoxybenzoyl                                                                         2,4-dichloro                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              207  2-chlorobenzoyl                                                                          2,6-dichloro                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              208  2-chlorobenzoyl                                                                          2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              209  2-chlorobenzoyl                                                                          2,5-difluoro                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              210  2-chlorobenzoyl                                                                          4-methoxy  .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              211  2-chlorobenzoyl                                                                          2-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              214  2-chlorobenzoyl                                                                          2,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              215  2-chlorobenzoyl                                                                          3-methoxy  .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              216  2-chlorobenzoyl                                                                          3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              217  2-chlorobenzoyl                                                                          2-trifluoromethyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              218  2-chlorobenzoyl                                                                          3-trifluoromethyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              219  2-chlorobenzoyl                                                                          4-trifluoromethyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              224  2-chlorobenzoyl                                                                          4-cyanobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              225  2-chlorobenzoyl                                                                          4-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              226  2-chlorobenzoyl                                                                          4-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              227  2-chlorobenzoyl                                                                          4-chloro   .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              228  2-chlorobenzoyl                                                                          2-methoxy  .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              229  2-chlorobenzoyl                                                                          4-nitro    .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              230  2-chlorobenzoyl                                                                          2-fluoro   .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              231  2-chlorobenzoyl                                                                          2,6-difluoro                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              235  3-methoxybenzoyl                                                                         2,5-difluoro                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              236  3-methoxybenzoyl                                                                         4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              237  3-methoxybenzoyl                                                                         3,4-dichloro                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              238  3-methoxybenzoyl                                                                         benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              239  3-methoxybenzoyl                                                                         3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              240  3-methoxybenzoyl                                                                         3,4-dichloro                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              241  3-methoxybenzoyl                                                                         4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              242  3-methoxybenzoyl                                                                         2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              243  benzoylchloride                                                                          4-trifluoromethoxy                                                                        .sub.- t-butylhydrazine                                                                pyridine                                                                             pyridine                                              benzoylchloride                                                                          hydrochloride                                         244  4-trifluoromethoxy                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              245  4-trifluoromethoxy                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              246  4-trifluoromethoxy                                                                       4-chloro benzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              247  4-trifluoromethoxy                                                                       3,4-dichloro                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              248  4-trifluoromethoxy                                                                       4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              249  4-trifluoromethoxy                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              251  4-ethoxybenzoyl                                                                          3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              252  4-ethoxybenzoyl                                                                          3,5-dimethyl                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              253  4-ethoxybenzoyl                                                                          benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              254  4-ethoxybenzoyl                                                                          2-nitro-4-chloro                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              255  3-chloro-4-methoxy-                                                                      benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              256  4-methylthio                                                                             benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              257  4- -n-butyloxy                                                                           4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              258  2-methylthio-                                                                            benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              259  2-nitro-4-chloro-                                                                        benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              261  2-nitro-4-chloro-                                                                        4- .sub.- t-butylbenzoyl                                                                  .sub.- t-butylhydrazine                                                                triethyl-                                                                            methylene                                   benzoylchloride                                                                          chloride  hydrochloride                                                                           amine chloride                               262  2-nitro-4-chloro-                                                                        4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              263  4-toluoyl chloride                                                                       2-chloro-5-methyl                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              265  4-phenoxybenzoyl                                                                         benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              266  4-phenoxybenzoyl                                                                         4-toluoyl chloride                                                                        .sub. - t-butylhydrazine                                                               sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              267  4- -n-butylbenzoyl                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              268  4- -n-butylbenzoyl                                                                       4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              269  4-isopropylbenzoyl                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              270  4-isopropylbenzoyl                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              272  4-cyanobenzoyl                                                                           benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              273  4-cyanobenzoyl                                                                           3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              274  2-methyl-4-chloro-                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              275  4-ethylbenzoyl                                                                           4-trifluoromethoxy                                                                        .sub.- t-butylhydrazine                                                                pyridine                                                                             pyridine                                    chloride  benzoylchloride                                                                          hydrochloride                                         276  benzoylchloride                                                                          2,3,4,5,6-penta-                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               fluoro benzoyl                                                                           hydrochloride                                                                           hydroxide                                                                            and water                                             chloride                                                        277  2,3,4,5,6-penta-                                                                         benzoylchloride                                                                            .sub.- t-butylhydrazine                                                               sodium                                                                               toluene                                     fluoro benzoyl      hydrochloride                                                                           hydroxide                                                                            and water                                   chloride                                                                  278  4-cyanobenzoyl                                                                           3,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              279  2-methyl-4-chloro-                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              280  4-trifluoromethyl                                                                        3,5-dimethylbenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              281  2-methyl-4-chloro-                                                                       3,5-dimethylbenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              282  benzoylchloride                                                                          3-vinylbenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              283  4-ethylbenzoyl                                                                           3-vinylbenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              284  4-trifluoromethyl-                                                                       3-vinylbenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              287  4- -n-propylbenzoyl                                                                      3,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              288  4- -n-propylbenzoyl                                                                      3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              290  4-vinylbenzoyl                                                                           3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              291  2,6-difluoro-                                                                            3,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              292  2,6-difluoro-                                                                            3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              296  4-chlorobenzoyl                                                                          2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              297  4-toluoyl chloride                                                                       3-toluoyl chloride                                                                       2,2-dimethyl-                                                                           sodium                                                                               toluene                                                         propylhydrazine                                                                         hydroxide                                                                            and water                                                       oxalic acid salt                                      299  4-chlorobenzoyl                                                                          3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              300  3-methoxybenzoyl                                                                         3,5-dimethylbenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              301  4-chlorobenzoyl                                                                          4-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              302  4- -n-propylbenzoyl                                                                      3,5-dimethylbenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              303  4-vinylbenzoyl                                                                           3,5-dimethylbenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              304  4-acetoxybenzoyl                                                                         3,5-dimethylbenzoyl                                                                        .sub.- t-butylhydrazine                                                               sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           bicarb-                                                                              and water                                                                onate                                        305  3,5-dimethyl-                                                                            benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              306  3,5-dimethyl-                                                                            3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              307  3,5-dimethyl-                                                                            4-ethylbenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              309  4-isopropyl-                                                                             3,5-dimethyl                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              310  4-ethylbenzoyl                                                                           2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              311  3-chloro-4-methyl-                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              312  3-chloro-4-methyl-                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              313  3-chloro-4-methyl-                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              314  3-chloro-4-methyl-                                                                       3,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              315  4-ethylbenzoyl                                                                           2-nitrobenzoyl                                                                           2,2-dimethyl-                                                                           sodium                                                                               toluene                                     chloride  chloride  propylhydrazine                                                                         hydroxide                                                                            and water                                                       oxalic acid salt                                      316  2,6-difluoro-                                                                            2-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              317  2,6-difluoro-                                                                            3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              318  2,6-difluoro-                                                                            4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              319  2,6-difluoro-                                                                            3,5-dimethylbenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              320  4-ethylbenzoyl                                                                           3,5-dimethylbenzoyl                                                                      2,2-dimethyl-                                                                           sodium                                                                               toluene                                     chloride  chloride  propylhydrazine                                                                         hydroxide                                                                            and water                                                       oxalic acid salt                                      321  3-trifluoromethyl-                                                                       4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              322  3-trifluoromethyl-                                                                       3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              325  2-nitro-3-methoxy-                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              327  4-chlorobenzoyl                                                                          4-carboxymethyl-                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              328  4-ethylbenzoyl                                                                           4-carboxymethyl-                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              334  4-ethylbenzoyl                                                                           3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              341  4-chlorobenzoyl                                                                          2-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              342  4-ethylbenzoyl                                                                           3,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              343  4-ethylbenzoyl                                                                           2-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              346  4-carboxymethyl-                                                                         4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           bicar-                                                                               and water                                                                bonate                                       347  4-carboxymethyl-                                                                         3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           bicar-                                                                               and water                                                                bonate                                       348  4-carboxymethyl-                                                                         3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           bicar-                                                                               and water                                                                bonate                                       355  3-phenoxybenzoyl                                                                         benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              356  3-phenoxybenzoyl                                                                         3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              357  4-acetylbenzoyl                                                                          3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              370  4-biphenylbenzoyl                                                                        3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              371  3-cyanobenzoyl                                                                           3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              377  3-chloromethyl-                                                                          3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              378  4-ethylbenzoyl                                                                           2,3-dimethylbenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              380  benzoylchloride                                                                          2,3-dimethylbenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              381  4-toluoyl chloride                                                                       2,3-dimethylbenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              387  benzoylchloride                                                                          1-naphthoyl                                                                               .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              407  2-naphthoyl                                                                              3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              408  benzoylchloride                                                                          3-trifluoromethoxy-                                                                       .sub.- t-butylhydrazine                                                                pyridine                                                                             pyridine                                              benzoylchloride                                                                          hydrochloride                                         409  4-isothiocyanato-                                                                        benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              410  2,6-difluoro-                                                                            2,4-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              411  2,6-difluoro-                                                                            3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              412  4-toluoyl 3,5-bis-(trifluoro-                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  methyl)benzoyl                                                                           hydrochloride                                                                           hydroxide                                                                            and water                                             chloride                                                        413  benzoylchloride                                                                          3,5-bis-(trifluoro-                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               methyl)benzoyl                                                                           hydrochloride                                                                           hydroxide                                                                            and water                                             chloride                                                        419  benzoylchloride                                                                          3-chloro-4-fluoro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              420  4-chlorobenzoyl                                                                          3-chloro-4-fluoro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              422  4-chlorobenzoyl                                                                          3,5-bis-(trifluoro-                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  methyl)benzoyl                                                                           hydrochloride                                                                           hydroxide                                                                            and water                                             chloride                                                        423  2,3-dimethyl-                                                                            3,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              388  1-naphthoyl                                                                              3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              389  4-isothiocyanato-                                                                        3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              392  2-fluorobenzoyl                                                                          2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              393  2-fluorobenzoyl                                                                          3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              395  2-fluorobenzoyl                                                                          2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              396  2-fluorobenzoyl                                                                          benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              401  4-bromobenzoyl                                                                           benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              402  2,3-dichloro-                                                                            2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              403  2,3-dichloro-                                                                            benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              404  2-fluorobenzoyl                                                                          3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              405  2,3-dichloro-                                                                            3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              406  benzoylchloride                                                                          2-naphthoyl                                                                               .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              424  4-toluoyl chloride                                                                       3-chloro-2-methyl-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              426  2,6-dimethyl-                                                                            3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              427  2,6-dimethyl-                                                                            3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              428  2,3-dimethyl-                                                                            2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              429  2,3-dimethyl-                                                                            3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              430  2,3-dimethyl-                                                                            3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              431  3-trifluoro-                                                                             benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     methoxybenzoyl      hydrochloride                                                                           hydroxide                                                                            and water                                   chloride                                                                  432  3-trifluoro-                                                                             3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     methoxybenzoyl      hydrochloride                                                                           hydroxide                                                                            and water                                   chloride                                                                  433  2,3-dimethyl-                                                                            2-methyl-3-chloro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              437  2,6-difluoro-                                                                            2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              438  2-methyl-3-chloro-                                                                       3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              439  2-methyl-3-chloro-                                                                       3-chloro-4-fluoro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              440  2,3-dimethyl-                                                                            3-chloro-4-fluoro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              441  4-ethylbenzoyl                                                                           3-chloro-4-fluoro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              442  3,4-dimethyl                                                                             benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              443  3,4-dimethyl-                                                                            3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              444  3,4-dimethyl-                                                                            2-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              445  3,4-dimethyl-                                                                            2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              446  3,4-dimethyl-                                                                            2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              447  3,4-dimethyl-                                                                            3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              448  3,4-dimethyl-                                                                            2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              450  benzoylchloride                                                                          3,4-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              451  4-ethylbenzoyl                                                                           3,4-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              452  2-fluoro-6-chloro-                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              454  4-chloromethyl                                                                           benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              455  2,3-dimethoxy-                                                                           benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              456  2,3-dimethoxy-                                                                           4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              457  2,3-dimethoxy-                                                                           2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              459  4- .sub.- t-butylbenzoyl                                                                 3,4-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              460  4- .sub.- t-butylbenzoyl                                                                 3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              461  4- .sub.- t-butylbenzoyl                                                                 2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              462  4- .sub.- t-butylbenzoyl                                                                 2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           bicar-                                                                               and water                                                                bonate                                       463  4- .sub.- t-butylbenzoyl                                                                 2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              464  4- .sub.- t-butylbenzoyl                                                                 3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              465  4- .sub.- t-butylbenzoyl                                                                 2-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              466  4- .sub.- t-butylbenzoyl                                                                 3,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              467  3,4-dimethyl-                                                                            3,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              468  3,4-dimethyl-                                                                            4-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              469  4- .sub.- t-butylbenzoyl                                                                 4-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              474  1-naphthoyl                                                                              2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              475  1-naphthoyl                                                                              2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              476  2-methyl-3-nitro-                                                                        benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              477  2-methyl-3-nitro-                                                                        3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              478  2-methyl-3-nitro-                                                                        4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              479  2-methyl-3-nitro-                                                                        2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              480  3-bromo-2-methyl-                                                                        benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              481  3-bromo-2-methyl-                                                                        3-toluoylchloride                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              482  3-bromo-2-methyl-                                                                        4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              483  3-bromo-2-methyl-                                                                        2,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              485  2-toluoyl chloride                                                                       2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              486  2-toluoyl chloride                                                                       2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           bicar-                                                                               and water                                                                bonate                                       487  2-toluoyl chloride                                                                       3-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              488  2-toluoyl chloride                                                                       4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              489  2-toluoyl chloride                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                                         hydrochloride                                                                           hydroxide                                                                            and water                              490  2-toluoyl chloride                                                                       3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              491  2-toluoyl chloride                                                                       3,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              492  2-toluoyl chloride                                                                       3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              493  2-methyl-3-fluoro-                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              494  2-methyl-3-fluoro-                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              495  2-fluoro-6-chloro-                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              496  2-fluoro-6-chloro-                                                                       2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              497  2-fluoro-6-chloro-                                                                       4-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              498  4-(2-chloroethyl)-                                                                       3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              499  2,4,6-trifluoro-                                                                         benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              500  2,4,6-trifluoro-                                                                         2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              501  2,4,6-trifluoro-                                                                         2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              502  2,4,6-trifluoro-                                                                         3,5-dimethyl                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              503  2-nitro-3-chloro-                                                                        benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              504  2-nitro-3-chloro-                                                                        2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              505  2-nitro-3-chloro-                                                                        2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              506  2-nitro-3-chloro-                                                                        3-toluoyl  .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              507  2-nitro-3-chloro-                                                                        3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              508  2-nitro-3-chloro-                                                                        2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              509  2-nitro-3-chloro-                                                                        3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                    510  2-nitro-3-chloro-                                                                        3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                    511  4-ethylbenzoyl                                                                           2,3-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                    512  4-ethylbenzoyl                                                                           2,3-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                    513  2,3-difluoro-                                                                            benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                    514  2,3-dichloro-                                                                            2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                    515  benzoylchloride                                                                          2,3-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                    516  2,3-dichloro-                                                                            3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              517  2,3-dichloro-                                                                            2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              518  2,3-dichloro-                                                                            3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              519  2,3-dichloro-                                                                            3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              520  2,3-dichloro-                                                                            2,3-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              521  2,3-difluoro-                                                                            2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              522  2,3-dimethyl-                                                                            4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              523  2,3-dimethyl-                                                                            2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              524  2,3-dimethyl-                                                                            2,6-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              525  2,3-dimethyl-                                                                            2,4-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              526  2,3-dimethyl-                                                                            3-methoxybenzoyl                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              527  2,3-dimethyl-                                                                            2-methoxybenzoyl                                                                           .sub.- t-butylhydrazine                                                               sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              528  2,3-dimethyl-                                                                            2-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              529  2,3-dimethyl-                                                                            4-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              530  2-methyl-3-chloro-                                                                       2,4-dichlorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              531  4-(2-chloro-                                                                             benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     ethyl)benzoyl       hydrochloride                                                                           hydroxide                                                                            and water                                   chloride                                                                  532  4-(2-chloro-                                                                             2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     ethyl)benzoyl                                                                            benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                                   chloride                                                                  533  3-fluoro-4-methyl-                                                                       3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              534  3-fluoro-4-methyl-                                                                       3,5-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              535  3-fluoro-4-methyl-                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              536  3-fluoro-4-methyl-                                                                       3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              537  3-fluoro-4-methyl-                                                                       2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              538  3-fluoro-4-methyl-                                                                       2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              539  4-ethylbenzoyl                                                                           3,5-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              540  2,3-dimethyl-                                                                            2-iodobenzoyl                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              542  2,6-difluoro-3-                                                                          benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     methylbenzoyl       hydrochloride                                                                           hydroxide                                                                            and water                                   chloride                                                                  543  2,6-difluoro-3-                                                                          3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     methylbenzoyl       hydrochloride                                                                           hydroxide                                                                            and water                                   chloride                                                                  544  2,6-difluoro-3-                                                                          2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     methylbenzoyl                                                                            benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                                   chloride                                                                  545  4-chlorobenzoyl                                                                          2,3-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              548  2-fluoro-6-chloro-                                                                       2,3-difluorobenzoyl                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              549  2,3-difluoro-                                                                            2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              550  2,3-difluoro-                                                                            3-toluoyl chloride                                                                        .sub.-  t-butylhydrazine                                                               sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              551  2,3-difluoro-                                                                            3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              552  2,3-difluoro-                                                                            2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              553  2,3-dimethyl-                                                                            2,3-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              554  2,3-dimethyl-                                                                            2,3-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              555  2,3-dimethyl-                                                                            3,4-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              556  2,3-dimethyl-                                                                            2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              557  4-ethylbenzoyl                                                                           2-methyl-5-chloro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              558  2,3-dimethyl-                                                                            benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              559  benzoylchloride                                                                          2-methyl-5-chloro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              560  2,6-difluoro-                                                                            2-methyl-5-chloro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              561  2,3-dimethyl-                                                                            2-methyl-5-chloro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              562  2-methyl-3-chloro-                                                                       2-methyl-5-chloro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              563  2,6-difluoro-                                                                            2-chloro-5-methyl-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              564  2,3-dimethyl-                                                                            2-chloro-5-methyl-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              565  2-methyl-3-chloro-                                                                       2-chloro-5-methyl-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              566  4-chlorobenzoyl                                                                          2-methyl-5-chloro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              567  4-chlorobenzoyl                                                                          2-chloro-5-methyl-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              568  2-fluoro-4-chloro-                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              569  2-fluoro-4-chloro-                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              570  2-fluoro-4-chloro-                                                                       3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              571  2-fluoro-4-chloro-                                                                       3,5-dichloro-                                                                             .sub.-  t-butylhydrazine                                                               sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              572  2-fluoro-4-chloro-                                                                       2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              573  2-fluoro-4-chloro-                                                                       2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              574  2-chloro-3-methyl-                                                                       2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              575  2-chloro-3-methyl-                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              576  2-chloro-3-methyl-                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              577  2-chloro-3-methyl-                                                                       3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              578  2-chloro-3-methyl-                                                                       3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              579  2-bromo-3-methyl-                                                                        3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              580  2-bromo-3-methyl-                                                                        2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              581  2-bromo-3-methyl-                                                                        3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              582  2-bromo-3-methyl-                                                                        3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              583  2-bromo-3-methyl-                                                                        2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              584  2,3-dimethyl-                                                                            2-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              585  2,3-dimethyl-                                                                            2-trifluoromethyl-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              586  2,3-dimethyl-                                                                            4-ethylbenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              587  2,3-dimethyl-                                                                            3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              588  2,6-difluoro-                                                                            3-chloro-4-fluoro-                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              589  4-chlorobenzoyl                                                                          3,5-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              590  2,3-dimethyl-                                                                            3,5-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              591  2-methyl-3-chloro-                                                                       3,5-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              592  benzoylchloride                                                                          3,5-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              593  4-ethylbenzoyl                                                                           2,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              594  2,6-difluoro-                                                                            3,5-difluoro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              595  2-methyl-3-chloro-                                                                       3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              596  2,3-dimethyl-                                                                            2,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              597  2-bromobenzoyl                                                                           3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              598  2-bromo-3-methyl-                                                                        3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              599  2-chloro-3-methyl-                                                                       3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              600  2-chloro-3-methyl-                                                                       3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              601  2-chloro-3-methyl-                                                                       2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              602  2,3-dimethyl-                                                                            2-nitro-3-methyl-                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              603  2,3-dimethyl-                                                                            2-nitro-5-methyl-                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              604  2,6-difluoro-                                                                            benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              605  2,6-dimethyl-                                                                            2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              606  2,4,6-trimethyl-                                                                         3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              607  2,4,6-trimethyl-                                                                         2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              608  2,6-difluoro-                                                                            4-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              609  2,6-difluoro-                                                                            2,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              610  2,4,6-trimethyl-                                                                         4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              611  2,4,6-trimethyl-                                                                         3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              612  2,4,6-trimethyl-                                                                         3,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              615  2,4-dimethyl-                                                                            3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride     hydrochloride                                                                           hydroxide                                                                            and water                              616  2,4-dimethyl-                                                                            2,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              617  2,4-dimethyl-                                                                            3,5-dimethyl-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              618  2,4-dimethyl-                                                                            3,5-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              619  2,4-dimethyl-                                                                            3-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              620  2,4-dimethyl-                                                                            3,4-dichloro-                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              621  2-bromo-3-methyl-                                                                        2-nitrobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              622  piperonyl chloride                                                                       benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                                         hydrochloride                                                                           hydroxide                                                                            and water                              623  piperonyl chloride                                                                       4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloride  hydrochloride                                                                           hydroxide                                                                            and water                              624  piperonyl chloride                                                                       3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                                         hydrochloride                                                                           hydroxide                                                                            and water                              626  2-pyrrolobenzoyl                                                                         benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              627  2-pyrrolobenzoyl                                                                         3-toluoyl chloride                                                                        .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              628  2,3-dimethyl-                                                                            2-bromo-5-methyl-                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          benzoylchloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              629  2-methyl-3-chloro-                                                                       3-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              630  2-methyl-3-chloro-                                                                       4-fluorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              631  2-methyl-3-chloro-                                                                       2-bromobenzoyl                                                                            .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chloride  hydrochloride                                                                           hydroxide                                                                            and water                              633  2-methyl-3-chloro-                                                                       3,5-dimethyl-4-                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          chlorobenzoyl                                                                            hydrochloride                                                                           hydroxide                                                                            and water                                             chloride                                                        929   -n-pentanoyl                                                                            2-furoylchloride                                                                          .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride            hydrochloride                                                                           hydroxide                                                                            and water                              930  ethylchloroformate                                                                        -n-pentanoylchloride                                                                     .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                                         hydrochloride                                                                           hydroxide                                                                            and water                              931  ethylchloroformate                                                                       4-chlorobenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                                         hydrochloride                                                                           hydroxide                                                                            and water                              932  benzoylchloride                                                                          ethylchoro                                                                                .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               formate   hydrochloride                                                                           hydroxide                                                                            and water                              934  phenylchloro-                                                                            benzoylchloride                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     formate             hydrochloride                                                                           hydroxide                                                                            and water                              935  benzoylchloride                                                                          phenylchloro                                                                              .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               formate   hydrochloride                                                                           hydroxide                                                                            and water                              936  benzoylchloride                                                                          4-nitrophenyl                                                                             .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               chloroformate                                                                            hydrochloride                                                                           hydroxide                                                                            and water                              940  4-ethylbenzoyl                                                                           phenylpropiolyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              945  4-chlorobenzoyl                                                                          4-phenylbenzoyl                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  chloride  hydrochloride                                                                           hydroxide                                                                            and water                              946  benzoylchloride                                                                          1,2,3,4-tetrahydro-                                                                       .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               2-naphthoylchloride                                                                      hydrochloride                                                                           hydroxide                                                                            and water                              947  prolinecarboxylic                                                                        3-toluoylchloride                                                                         .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     acid chloride       hydrochloride                                                                           hydroxide                                                                            and water                              952  benzoylchloride                                                                          N,N-diethylcar-                                                                           .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               bamoyl chloride                                                                          hydrochloride                                                                           hydroxide                                                                            and water                              953  benzoylchloride                                                                          p-chlorophenyl                                                                            .sub.- t-butylhydrazine                                                                none  methylene                                             isocyanate                                                                               hydrochloride  chloride                               962  3,5-dichlorobenzoyl                                                                      chloroacetyl                                                                             phenylhydrazine                                                                         sodium                                                                               toluene                                     chloride  chloride           hydroxide                                                                            and water                              966  3,5-dichlorobenzoyl                                                                      chloracetyl                                                                              benzylhydrazine                                                                         sodium                                                                               toluene                                     chloride  chloride           hydroxide                                                                            and water                              993   -n-pentanoyl                                                                            ethylchloro                                                                               .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                               formate   hydrochloride                                                                           hydroxide                                                                            and water                              994  4-chlorobenzoyl-                                                                         ethylchloro                                                                               .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     chloride  formate   hydrochloride                                                                           hydroxide                                                                            and water                              995  2,6-difluoro-                                                                            ethylchloro                                                                               .sub.- t-butylhydrazine                                                                sodium                                                                               toluene                                     benzoylchloride                                                                          formate   hydrochloride                                                                           hydroxide                                                                            and water                              997  benzoylchloride                                                                          3-chlorobenzoyl                                                                          N'-(1,1-di-                                                                             sodium                                                                               toluene                                               chloride  methyl)benzyl-N-                                                                        hydroxide                                                                            and water                                                       benzoyl                                                                        hydrazine                                             998  benzoylchloride                                                                          2,3-dichloro-                                                                            N'-(1,1-di-                                                                             sodium                                                                               toluene                                               benzoylchloride                                                                          methyl)benzyl-N-                                                                        hydroxide                                                                            and water                                                       benzoyl                                                                        hydrazine                                             __________________________________________________________________________

By following substantially the procedures in Example 44 and using the reactants shown below in Table IV, the products of Example Nos. 39, 46, 63, 110, 111, 112, 114, 115, 116, 120, 124, 127, 128, 129, 136, 143, 155 through 158, 185 through 189, 332, 336 through 340, 382, 383, 384, 399, 400, 414 through 418, 421, 435, 436, 453, 470, 471, 472, 546, 547, 634 and 955 through 960 were prepared.

                  TABLE IV                                                         ______________________________________                                         Ex.                                                                            No.  Reactants                                                                 ______________________________________                                          39  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Dimethyl ketone                                              Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            acetone                                                      Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-isopropyl-1-benzoyl-                                                         hydrazine                                                    Compound of Formula VI:                                                                          Benzoylchloride                                              Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                        46  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VII:                                                                         Methylethyl ketone                                           Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            2-butanone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-sec-butyl-1-benzoyl-                                                         hydrazine                                                    Compound of Formula VI:                                                                          Benzoylchloride                                              Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                        63  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Methyl- .sub.- t-butyl ketone                                Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            methyl-t-butylketone                                         Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-(1,2,2-trimethylpropyl)-1-                                                   benzoylhydrazine                                             Compound of Formula VI:                                                                          Benzoylchloride                                              Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       110  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        1,1,1-trimethylacetaldehyde                                  Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of 1,1,1-                                                     trimethylacetaldehyde                                        Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-neopentyl-1-benzoyl-                                                         hydrazine                                                    Compound of Formula VI:                                                                          2-bromobenzoylchloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       111  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        1,1,1-trimethylacetaldehyde                                  Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of 1,1,1-                                                     trimethylacetaldehyde                                        Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-neopentyl-1-benzoyl-                                                         hydrazine                                                    Compound of Formula VI:                                                                          2-nitrobenzoylchloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       112  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        1,1,1-trimethylacetaldehyde                                  Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of 1,1,1-                                                     trimethylacetaldehyde                                        Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-neopentyl-1-benzoyl-                                                         hydrazine                                                    Compound of Formula VI:                                                                          2-anisoyl chloride                                           Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       114  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Isobutyraldehyde                                             Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            isobutyraldehyde                                             Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-isobutyl-1-benzoyl-                                                          hydrazine                                                    Compound of Formula VI:                                                                          Benzoylchloride                                              Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       115  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Acetone                                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            acetone                                                      Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-isopropyl-1-benzoyl-                                                         hydrazine                                                    Compound of Formula VI:                                                                          2-bromobenzoylchloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       116  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Acetone                                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            acetone                                                      Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-isopropyl-1-benzoyl-                                                         hydrazine                                                    Compound of Formula VI:                                                                          3,4-dichlorobenzoylchloride                                  Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       120  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Dicyclopropylketone                                          Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            dicyclopropylketone                                          Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-dicyclopropylmethyl-1-                                                       benzoylhydrazine                                             Compound of Formula VI:                                                                          Benzoylchloride                                              Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       124  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Methyl- .sub.- t-butyl ketone                                Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            methyl- .sub.- t-butylketone                                 Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-(1,2,2-trimethylpropyl)-1-                                                   benzoylhydrazine                                             Compound of Formula VI:                                                                          2-nitrobenzoylchloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       127  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Methyl- .sub.- t-butyl ketone                                Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            methyl- .sub.- t-butylketone                                 Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-(1,2,2-trimethylpropyl)-1-                                                   benzoylhydrazine                                             Compound of Formula VI:                                                                          Benzoylchloride                                              Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       128  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Diisopropyl ketone                                           Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            diisopropylketone                                            Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-diisopropylmethyl-1-                                                         benzoylhydrazine                                             Compound of Formula VI:                                                                          Benzoylchloride                                              Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       129  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Cyclopropylmethyl ketone                                     Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            cyclopropylmethylketone                                      Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-(1-cyclopropylethyl)-1-                                                      benzoylhydrazine                                             Compound of Formula VI:                                                                          Benzoylchloride                                              Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       136  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Methyl- .sub.- t-butyl ketone                                Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            methyl- .sub.- t-butylketone                                 Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           2-(1-methyl)neopentyl-1-                                                       benzoylhydrazine                                             Compound of Formula VI:                                                                          2-bromobenzoylchloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       143  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Methyl cyclohexyl ketone                                     Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of methyl                                                     cyclohexyl ketone                                            Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-benzoyl-2-(1-cyclohexyl-                                                     ethyl)hydrazine                                              Compound of Formula VI:                                                                          benzoylchloride                                              Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       155  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Acetone                                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            acetone                                                      Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-benzoyl-2-isopropyl                                                          hydrazine                                                    Compound of Formula VI:                                                                          2,6-dichlorobenzoylchloride                                  Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       156  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Trimethylacetaldehyde                                        Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            trimethylacetaldehyde                                        Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-benzoyl-2-(2,2-dimethyl-                                                     propyl)hydrazine                                             Compound of Formula VI:                                                                          3,4-dichlorobenzoylchloride                                  Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       157  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-benzoyl-2-(1,2,2-trimethyl-                                                  propyl)hydrazine                                             Compound of Formula VI:                                                                          4-cyanobenzoylchloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       158  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Trimethylacetaldehyde                                        Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            trimethyl acetaldehyde                                       Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-benzoyl-2-(2,2-dimethyl-                                                     propyl)hydrazine                                             Compound of Formula VI:                                                                          4-ethylbenzoylchloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       185  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-benzoyl-2-(1,2,2-tri-                                                        methylpropyl)hydrazine                                       Compound of Formula VI:                                                                          3-nitrobenzoylchloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       186  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Trimethylacetaldehyde                                        Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            trimethyl acetaldehyde                                       Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-benzoyl-2-(2,2-dimethyl-                                                     propyl)hydrazine                                             Compound of Formula VI:                                                                          3-nitrobenzoylchloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       187  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Trimethylacetaldehyde                                        Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            trimethyl acetaldehyde                                       Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-benzoyl-2-(2,2-dimethyl-                                                     propyl)hydrazine                                             Compound of Formula VI:                                                                          3-toluoyl chloride                                           Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       188  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Trimethylacetaldehyde                                        Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            trimethyl acetaldehyde                                       Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-benzoyl-2-(2,2-dimethyl-                                                     propyl)hydrazine                                             Compound of Formula VI:                                                                          4-chlorobenzoylchloride                                      Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       189  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Trimethylacetaldehyde                                        Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            trimethyl acetaldehyde                                       Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-benzoyl-2-(2,2-dimethyl-                                                     propyl)hydrazine                                             Compound of Formula VI:                                                                          2,4-dinitrobenzoylchloride                                   Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       332  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(1,2,2-                                                        trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          2-nitrobenzoylchloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       336  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(1,2,2-                                                        trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          3,5-dimethylbenzoylchloride                                  Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       337  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(1,2,2-                                                        trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          2-nitro-3-methyl benzoyl                                                       chloride                                                     Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       338  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(1,2,2-                                                        trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          2-nitro-5-methylbenzoyl                                                        chloride                                                     Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       339  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(1,2,2-                                                        trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          3-toluoyl chloride                                           Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       340  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(1,2,2-                                                        trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          2-iodobenzoyl chloride                                       Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       382  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(1,2,2-                                                        trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          2-toluoyl chloride                                           Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       383  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(1,2,2-                                                        trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          2-trifluoromethylbenzoyl                                                       chloride                                                     Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       384  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(1,2,2-                                                        trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          benzoyl chloride                                             Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       399  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        4,4-dimethyl-2-pentanone                                     Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         3,4-dimethyl-2-pentanone                                     Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(4,4-                                                          dimethyl-2-pentyl)hydrazine                                  Compound of Formula VI:                                                                          3,5-dimethylbenzoyl chloride                                 Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       400  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        4,4-dimethyl-2-pentanone                                     Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         4,4-dimethyl-2-pentanone                                     Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(4,4-                                                          dimethyl-2-pentyl)hydrazine                                  Compound of Formula VI:                                                                          3,4-dichlorobenzoyl chloride                                 Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       414  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        3-methyl-3-ethyl-2-pentanone                                 Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         3-methyl-3-ethyl-2-pentanone                                 Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(3-methyl-3-                                                   ethylpent-2-yl)hydrazine                                     Compound of Formula VI:                                                                          benzoyl chloride                                             Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       415  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        3-methyl-3-ethyl-2-pentanone                                 Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         3-methyl-3-ethyl-2-pentanone                                 Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(3-methyl-3-                                                   ethylpent-2-yl)hydrazine                                     Compound of Formula VI:                                                                          benzoyl chloride                                             Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       416  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        3-methyl-3-ethyl-2-pentanone                                 Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoyl hydrazone of                                                         3-methyl-3-ethyl-2-pentanone                                 Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(3-methyl-3-                                                   ethylpent-2-yl)hydrazine                                     Compound of Formula VI:                                                                          2-nitrobenzoyl chloride                                      Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       417  Compound of Formula VII:                                                                         4-ethylhydrazine                                             Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-ethylbenzoyl hydrazone of                                                    pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-ethylbenzoyl)-2-(1,2,2-                                                   trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          3,5-dimethylbenzoyl chloride                                 Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       418  Compound of Formula VII:                                                                         4-ethylbenzoyl hydrazine                                     Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-ethylbenzoyl hydrazone of                                                    pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-ethylbenzoyl)-2-(1,2,2-                                                   trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          2-nitro-5-methylbenzoyl                                                        chloride                                                     Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       421  Compound of Formula VII:                                                                         4-ethylbenzoyl hydrazine                                     Compound of Formula VIII:                                                                        Acetone                                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-ethylbenzoyl hydrazone of                                                    acetone                                                      Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-ethylbenzoyl)-2-                                                          isopropyl hydrazine                                          Compound of Formula VI:                                                                          3,5-dimethylbenzoyl chloride                                 Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       434  Compound of Formula VII:                                                                         4-ethylbenzoyl hydrazine                                     Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-ethylbenzoyl hydrazone of                                                    pinacolone                                                   Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-ethylbenzoyl)-2-(1,2,2-                                                   trimethylpropyl)hydrazine                                    Compound of Formula VI:                                                                          2,4-dichlorobenzoyl chloride                                 Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       435  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        3-methyl-3-ethyl-2-pentanone                                 Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoylhydrazone of                                                          3-methyl-3-ethyl-2-pentanone                                 Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(3-methyl-                                                     3-ethylpent-2-yl)hydrazine                                   Compound of Formula VI:                                                                          2-nitro-5-methylbenzoyl                                                        chloride                                                     Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       436  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        3-methyl-3-ethyl-2-pentanone                                 Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoylhydrazone of                                                          3-methyl-3-ethyl-2-pentanone                                 Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(3-methyl-                                                     3-ethylpent-2-yl)hydrazine                                   Compound of Formula VI:                                                                          2-nitro-5-methylbenzoyl                                                        chloride                                                     Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       453  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        2,2-dimethyl-3-pentanone                                     Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoylhydrazone of 2,2-                                                     dimethyl-3-pentanone                                         Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(2,2-dimethyl                                                  pent-3-yl)hydrazine                                          Compound of Formula VI:                                                                          Benzoyl chloride                                             Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       470  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        2,2-dimethyl-3-pentanone                                     Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoylhydrazone of 2,2-                                                     dimethyl-3-pentanone                                         Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(2,2-                                                          dimethylpent-3-yl)hydrazine                                  Compound of Formula VI:                                                                          2-nitrobenzoyl chloride                                      Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       471  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        2,2-dimethyl-3-butanone                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoylhydrazone of 2,2-                                                     dimethyl-3-pentanone                                         Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(2,2-                                                          dimethylpent-3-yl)hydrazine                                  Compound of Formula VI:                                                                          2-nitro-5-methylbenzoyl                                                        chloride                                                     Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       472  Compound of Formula VII:                                                                         4-toluoylhydrazine                                           Compound of Formula VIII:                                                                        2,2-dimethyl-3-pentanone                                     Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          4-toluoylhydrazone of 2,2-                                                     dimethyl-3-pentanone                                         Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(4-toluoyl)-2-(2,2-                                                          dimethylpent-3-yl)hydrazine                                  Compound of Formula VI:                                                                          3,5-dimethylbenzoyl chloride                                 Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       546  Compound of Formula VII:                                                                         2,3-dimethylbenzoyl                                                            hydrazine                                                    Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          (2,3-dimthylbenzoyl)-                                                          hydrazone of pinacolone                                      Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(2,3-dimethylbenzoyl)-2-                                                     (1,2,2-trimethylpropyl)                                                        hydrazine                                                    Compound of Formula VI:                                                                          3,5-dimethylbenzoyl chloride                                 Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       547  Compound of Formula VII:                                                                         2,3-dimethylbenzoyl                                                            hydrazine                                                    Compound of Formula VIII:                                                                        Pinacolone                                                   Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula IX:                                                                          (2,3-dimethylbenzoyl)-                                                         hydrazone of pinacolone                                      Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Acetic acid                                                  Compound of Formula X:                                                                           1-(2,3-dimethylbenzoyl)-                                                       (1,2,2-trimethylpropyl)                                                        hydrazine                                                    Compound of Formula VI:                                                                          3-toluoyl chloride                                           Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       634  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Methyl- .sub.- t-butyl ketone                                Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula IX:                                                                          Benzoylhydrazone of methyl                                                      .sub.- t-butyl ketone                                       Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula X:                                                                           1-(1,2,2-trimethylpropyl)-2-                                                   benzoylhydrazine                                             Compound of Formula VI:                                                                          2-methyl-3-chlorobenzoyl                                                       chloride                                                     Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       955  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Deoxybenzoin                                                 Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            deoxybenzoin                                                 Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula X:                                                                           1-(1,2-diphenylethyl)-                                                         2-benzoylhydrazine                                           Compound of Formula VI:                                                                          3-toluoyl chloride                                           Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       956  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Cyclopentanone                                               Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            cyclopentanone                                               Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula X:                                                                           1-cyclopentyl-2-benzoyl                                                        hydrazine                                                    Compound of Formula VI:                                                                          3-toluoyl chloride                                           Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       957  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Cyclohexanone                                                Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula IX:                                                                          Benzoylhydrazone of                                                            Cyclohexanone                                                Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula X:                                                                           1-cyclohexyl-2-benzoyl                                                         hydrazine                                                    Compound of Formula VI:                                                                          3-toluoyl chloride                                           Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       958  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        2-methyl cyclohexanone                                       Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula IX:                                                                          Benzoyl hydrazone of                                                           2-methyl-cyclohexanone                                       Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula X:                                                                           1-(2-methylcyclohexyl)-                                                        2-benzoylhydrazine                                           Compound of Formula VI:                                                                          3-toluoyl chloride                                           Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       960  Compound of Formula VII:                                                                         Benzoylhydrazine                                             Compound of Formula VIII:                                                                        Phenylcyclopentyl ketone                                     Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula IX:                                                                          Benzoylhydrazone of phenyl-                                                    cyclopentylketone                                            Reducing Agent:   Sodium cyanoborohydride                                      Solvent:          Methanol                                                     Catalyst:         Hydrochloric acid                                            Compound of Formula X:                                                                           1-(alpha-cyclopentyl-                                                          benzyl)-2-benzoyl hydrazine                                  Compound of Formula VI:                                                                          3-toluoyl chloride                                           Base:             Sodium hydroxide                                             Solvent:          Toluene and water                                       ______________________________________                                    

By following substantially the procedures in Example 220 and using the reactants shown below in Table V, the products of Examples 168, 170, 171, 172, 191, 192, 193, 212, 213, 221 through 223, 232, 233, 293, 326, 331, 379, 397, 398, 425 and 458 were prepared.

                  TABLE V                                                          ______________________________________                                         Ex.  Compound of  Compound of          Sol-                                    No.  Formula XII  Formula XIII Base    vent                                    ______________________________________                                         168  3,4-dimethoxy-                                                                              N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   170  2-chloromethyl-                                                                             N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   171  4- -n-propylbenzoyl                                                                         N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      chloride     benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   172  2-nitrobenzoyl                                                                              N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      chloride     benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   191  3,4-dichloro-                                                                               N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            (4-chlorobenzoyl)                                                                           hydroxide                                                                              and                                                       hydrazine    water                                           192  4- -n-heptyl-                                                                               N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            (4-chlorobenzoyl)                                                                           hydroxide                                                                              and                                                       hydrazine            water                                   193  4- -n-propyl-                                                                               N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            (4-chlorobenzoyl)                                                                           hydroxide                                                                              and                                                       hydrazine            water                                   212  2-fluoro-    N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            (4-chlorobenzoyl)                                                                           hydroxide                                                                              and                                                       hydrazine            water                                   213  2,4-dichloro-                                                                               N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            (4-chlorobenzoyl)                                                                           hydroxide                                                                              and                                                       hydrazine            water                                   221  3-nitrobenzoyl                                                                              N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      chloride     benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   222  2,6-dichloro-                                                                               N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   223  2,4-difluoro-                                                                               N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   232  4-nitrobenzoyl                                                                              N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      chloride     benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   233  4-cyanobenzoyl                                                                              N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      chloride     benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   293  2-chloromethyl                                                                              N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            (4-chlorobenzoyl)                                                                           hydroxide                                                                              and                                                       hydrazine            water                                   326  3-bromo-4-methyl-                                                                           N'- .sub.- t-butyl-N'-                                                                      triethyl                                                                               meth-                                        benzoic methane-                                                                            benzoylhydrazine                                                                            amine   ylene                                        sulfonic anhydride                chlor-                                                                         ide                                     331  4-fluorobenzoyl                                                                             N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      chloride     benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   379  2,3-dimethyl N'- .sub.- t-butyl-N'                                                                       sodium  toluene                                      benzoylchloride                                                                             (3-toluoyl)- hydroxide                                                                              and                                                       hydrazine            water                                   397  2-methyl-3-chlor-                                                                           N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            (3-toluoyl)- hydroxide                                                                              and                                                       hydrazine            water                                   398  2-methyl-3-chloro-                                                                          N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   425  3-chloro-4-fluoro-                                                                          N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            benzoylhydrazine                                                                            hydroxide                                                                              and                                                                            water                                   458  3-chloro-4-fluoro-                                                                          N'- .sub.- t-butyl-N'-                                                                      sodium  toluene                                      benzoyl chloride                                                                            (3,4-dichloro-                                                                              hydroxide                                                                              and                                                       benzoyl)hydrazine    water                                   ______________________________________                                    

                                      TABLE VI                                     __________________________________________________________________________     Ex. No.                                                                             Compound of Formula II                                                                      Reactant                                                                              Base or Acid                                                                          Solvent                                        __________________________________________________________________________     162  N-benzoyl-N'- .sub.- t-butyl-                                                               sodium        methanol                                            N'-(4-formylbenzoyl)-                                                                       borohydride                                                       hydrazine                                                                 329  N-benzoyl-N'- .sub.- t-butyl-N'-                                                            zinc dust     acetic                                              (3-nitrobenzoyl)-          acid                                                hydrazine                                                                 330  N-benzoyl-N'- .sub.- t-butyl-N'-                                                            zinc dust     acetic                                              (2-nitrobenzoyl)-          acid                                                hydrazine                                                                 350  N-(2-nitro-3-methoxy-                                                                       zinc dust     acetic                                              benzoyl)-N'- .sub.- t-butyl-N'-                                                                           acid                                                (3-toluoyl)hydrazine                                                      351  N-(4-nitrobenzoyl)-N'-                                                                      hydrogen,     ethyl                                                .sub.- t-butyl-N'(4-chloro-                                                                platinum      acetate-                                            benzoyl)hydrazine                                                                           on carbon     methanol                                       352  N-(4-aminobenzoyl)-N'-                                                                      methyl pyridine                                                                              methylene                                            .sub.- t-butyl-N'-(4-chloro-                                                               chloro-       chloride                                            benzoyl)hydrazine                                                                           formate                                                      353  N-(4-aminobenzoyl)-N'-                                                                      acetic                                                             .sub.- t-butyl-N'-(4-chloro-                                                               anhydride                                                         benzoyl)hydrazine                                                         354  N-(2-nitro-3-methoxy-                                                                       1. H.sub.2 /catalyst                                                                         1. ethyl acetate                                    benzoyl)-N'- .sub.- t-butyl-                                                                2. AC.sub.2 O 2. none                                             N'-(3-toluoyl)hydrazine                                                   372  N-(3-nitrobenzoyl)-N'-                                                                      zinc          aqueous                                              .sub.- t-butyl-N'-(3-toluoyl)-                                                             dust          acetic                                              hydrazine                  acid                                           375  N-(3-aminobenzoyl)-N'-                                                                      methacryloyl                                                                          sodium water                                                .sub.- t-butyl-N'-(3-toluoyl)-                                                             chloride                                                                              hydroxide                                                  hydrazine                                                                 473  N-(2-nitro-3-mehtoxy-                                                                       zinc   amonium                                                                               aqueous                                             benzoyl)-N'- .sub.- t-butyl-N'-                                                             dust   chloride                                                                              ethanol                                             benzoylhydrazine                                                          484  N-(2-methyl-3-nitro                                                                         zinc   ammonium                                                                              aqueous                                             benzoyl)-N'- .sub.- t-butyl-N'-                                                             dust   chloride                                                                              ethanol                                             (3-toluoyl) hydrazine                                                     __________________________________________________________________________

Using a chloromethylbenzoyl compound of Formula II as a reactant and performing a substitution reaction under the conditions (base or acid, and solvent) set forth in Table VII, the products of Examples 159, 161, 162, 294, 361, 362, 363 and 367 were prepared.

                                      TABLE VII                                    __________________________________________________________________________     Ex. No.                                                                             Compound of Formula II                                                                      Reactant                                                                               Base or Acid                                                                          Solvent                                       __________________________________________________________________________     159  N-benzoyl-N'- .sub.- t-butyl-N'-                                                            sodium         N,N-                                               (3-chloromethylbenzoyl)                                                                     acetate        dimethyl-                                          hydrazine                   formamide                                     161  N-benzoyl-N'- .sub.- t-butyl-N'-                                                             -p-thiocersol                                                                         sodium toluene-                                           (3-chloromethylbenzoyl)                                                                             hydroxide                                                                             water                                              hydrazine                                                                 294  N-(2-chloromethyl-                                                                          diethylamine   tetra-                                             benzoyl)-N"- .sub.- t-butyl-                                                                               hydro-                                             N'-(4-chlorobenzoyl)-       furan                                              hydrazine                                                                 361  N-(4-chloromethyl                                                                           sodium         N,N-                                               benzoyl)N'- .sub.- t-butyl-N'-                                                              acetate        dimethyl-                                          benzoyl hydrazine           formamide                                     362  N-(4-chloromethyl                                                                           potassium      ethanol                                            benzoyl)-N'- .sub.- t-butyl-N'-                                                             thiocyanate                                                       benzoyl hydrazine                                                         363  N-(4-acetoxymethyl   sodium methanol                                           benzoyl)-N'- .sub.- t-butyl-N'-                                                                     hydroxide                                                 benzoylhydrazine                                                          367  N-(4-chloromethyl                                                                           potassium      dimethyl                                           benzoyl)-N'- .sub.- t-butyl-N'-                                                             cyanide        formamide                                          benzoyl hydrazine                                                         __________________________________________________________________________

Using an acetyloxybenzoyl compound of Formula II as a reactant and performing a hydrolysis, under the conditions (base and solvent) set forth in Table VIII, the products of Examples 151, 165, 203, 271, 285, 333, 349 and 614 were prepared.

                  TABLE VIII                                                       ______________________________________                                         Ex.  Compound of              Base or                                          No.  Formula II      Reactant Acid    Solvent                                  ______________________________________                                         151  N-benzoyl-N'- .sub.- t-butyl-                                                                           sodium  methanol                                      N'-(2-acetoxybenzoyl)-   hydroxide                                             hydrazine                                                                 165  N-benzoyl-N'-(1,2,2-     sodium  methanol                                      trimethylpropyl)-N'-     hydroxide                                             2-acetoxybenzoyl)                                                              hydrazine                                                                 203  N-benzoyl-N'- .sub.- t-butyl-N'-                                                                        potassium                                                                              methanol                                      (3-acetoxybenzoyl)       hydroxide                                             hydrazine                                                                 271  N-(4-acetoxybenzoyl)-    potassium                                                                              methanol                                      N'- .sub.- t-butyl-N'-benzoyl                                                                           hydroxide                                             hydrazine                                                                 285  N-(4-acetoxybenzoyl)-    potassium                                                                              methanol                                      N'- .sub.- t-butyl-N'-(3-toluoyl)                                                                       hydroxide                                             hydrazine                                                                 333  N-(3-acetoxybenzoyl)-    potassium                                                                              methanol                                      N'- .sub.- t-butyl-N'-benzoyl                                                                           hydroxide                                             hydrazine                                                                 349  N-(4-carbomethoxy        sodium  aqueous                                       benzoyl)-N'- .sub.- t-butyl-                                                                            hydroxide                                                                              tetra-                                        N'-(3-toluoyl)hydrazine          hydro-                                                                         furan                                    614  N,N'-bis-(2-acetoxy-     sodium  methanol                                      benzoyl)-N'- .sub.- t-butyl                                                                             hydroxide                                             hydrazine                                                                 ______________________________________                                    

Using a hydroxybenzoyl compound of Formula II as a reactant and performing an alkylation or esterification, under the conditions (base and solvent) set forth in Table IX, the products of Examples 144, 286, 335, 345, 358, 359, 360, 365, 366 and 385 were prepared.

                  TABLE IX                                                         ______________________________________                                         Ex.  Compound of                                                               No.  Formula II     Reactant  Base    Solvent                                  ______________________________________                                         144  N-benzoyl-N'- .sub.- t-butyl-                                                                 allyl     potassium                                                                              tetra-                                        N'-(4-hydroxybenzoyl)                                                                         bromide    .sub.- t-butoxide                                                                     hydro-                                        hydrazine                        furan                                    286  N-(4-hydroxybenzoyl)-                                                                         allyl     potassium                                                                              tetra-                                        N'- .sub.- t-butyl-N'-benzoyl-                                                                bromide    .sub.- t-butoxide                                                                     hydro-                                        hydrazine                        furan                                    335  N-(3-hydroxybenzoyl)-                                                                         allyl     sodium  dimethyl-                                     N'- .sub.- t-butyl-N'-benzoyl-                                                                bromide   hydride form-                                         hydrazine                        amide                                    345  N-(3-hydroxybenzoyl)-                                                                         vinyl     potassium                                                                              tetra-                                        N'- .sub.- t-butyl-N'-benzoyl-                                                                chloro-    .sub.- t-butoxide                                                                     hydro-                                        hydrazine      formate           furan                                    358  N-(4-hydroxybenzoyl)-                                                                         chloro-   potassium                                                                              tetra-                                        N'- .sub.- t-butyl-N'-benzoyl-                                                                methyl-    .sub.- t-butoxide                                                                     hydro-                                        hydrazine      methyl            furan                                                        ether                                                      359  N-(4-hydroxybenzoyl)-                                                                         N,N-di-   potassium                                                                              tetra-                                        N'- .sub.- t-butyl-N'-benzoyl-                                                                methyl-    .sub.- t-butoxide                                                                     hydro-                                        hydrazine      carbamoyl         furan                                                        chloride                                                   360  N-(4-hydroxybenzoyl)-                                                                         ethyl     potassium                                                                              tetra-                                        N'- .sub.- t-butyl-N'-benzoyl-                                                                bromo-     .sub.- t-butoxide                                                                     hydro-                                        hydrazine      acetate           furan                                    365  N-(4-hydroxybenzoyl)-                                                                         chloro-   sodium  dimethyl-                                     N'- .sub.- t-butyl-N'-benzoyl-                                                                methyl-   hydride form-                                         hydrazine      methyl            amide                                                        sulfide                                                    366  N-(4-hydroxybenzoyl)-                                                                         isobutyl  potassium                                                                              dimethyl                                      N'- .sub.- t-butyl-N'-benzoyl-                                                                bromide    .sub.- t-butoxide                                                                     form-                                         hydrazine                        amide                                    385  N-(4-hydroxybenzoyl)-                                                                         chloro-   potassium                                                                              tetra-                                        N'- .sub.- t-butyl-N'-benzoyl-                                                                methyl-    .sub.- t-butoxide                                                                     hydro-                                        hydrazine      methyl            furan                                                        ether                                                      ______________________________________                                    

Using a compound of Formula II as a reactant and performing the stated reaction under the conditions (additional reactant, base or acid, and solvent) set forth in Table X, the products of Examples 149, 164, 166, 368, 369, 373, 374, 376, 386 and 541 were prepared.

                  TABLE X                                                          ______________________________________                                                   Compound Prepared, Reactants, Reaction                               Example No.                                                                              Conducted and Conditions                                             ______________________________________                                         149       N-benzoyl-N'- .sub.- t-butyl-N'-(4-methane-                                    sulfonylbenzoyl)hydrazine was prepared from                                    N-benzoyl-N'- .sub.- t-butyl-N'-(4-                                            methylthiobenzoyl)hydrazine using meta-                                        chloroperbenzoic acid in methylene chloride                                    in an oxidation reaction.                                            164       N-benzoyl-N'- .sub.- t-butyl-N'-(4-carboxybenzoyl)-                            hydrazine was prepared from N-benzoyl-N'- .sub.- t-                            butyl-N'-(4-methoxycarbonyl-                                                   benzoyl)hydrazine sodium hydroxide as a                                        base and methanol as solvent in a                                              hydrolysis reaction.                                                 166       N-benzoyl-N'- .sub.- t-butyl-N'-(4-(2,2-                                       dichloroethenyl)benzoyl)hydrazine was                                          prepared from N-benzoyl-N'- .sub.- t-butyl-N'-                                 (4-formylbenzoyl)hydrazine using                                               triphenylphosphine in carbon tetra-                                            chloride as solvent in a Witting-type                                          reaction.                                                            368       N-(4-(1,2-epoxypropyl)benzoyl)-N'- .sub.- t-butyl-                             N'-benzoylhydrazine was prepared from N-                                       (4-(1-propenyl)benzoyl)-N'- .sub.- t-butyl-N'-                                 benzoylhydrazine using meta-chloroperbenzoic                                   acid in methylene chloride as solvent in an                                    oxidation reaction.                                                  369       N-(4-acetylsemicarbazone)-N'- .sub.- t-butyl-                                  N-(3-toluoyl)hydrazine was prepared from N-                                    (4-acetylbenzoyl)-N'- .sub.- t-butyl-N'-(3-toluoyl)                            hydrazine using semicarbazide in ethanol                                       solvent with hydrochloric acid catalyst in                                     a condensation reaction.                                             373       N-(4-(2-hydroxy-1,1-dimethylethylamino-                                        carbonyl)benzoyl)-N'- .sub.- t-butyl-N'-(3-toluoyl)-                           hydrazine was prepared from N-(4-                                              methoxycarbonylbenzoyl)-N'- .sub.- t-butyl-N'-                                 (3-toluoyl)hydrazine using 2-amino-2-                                          methylpropanol in a condensation reaction.                           374       N-(4-(2-hydroxyethyl)benzoyl)-N'- .sub.- t-butyl-                              N'-(3-toluoyl)hydrazine was prepared from                                      N-(4-acetylbenzoyl)-N'- .sub.- t-butyl-N'-                                     (3-toluoyl)hydrazine using sodium borohydride                                  in methanol solvent in a reduction reaction.                         376       N-(3-carboxybenzoyl)-N'- .sub.- t-butyl-N'-                                    (3-toluoyl)hydrazine was prepared from                                         N-(3-cyanobenzoyl)-N'- .sub.- t-butyl-N'-(3-                                   toluoyl)hydrazine using potassium hydroxide                                    as base in methanol solvent in a                                               hydrolysis reaciton.                                                 386       N-(4-(1-methylethenyl)benzoyl)-N'- .sub.- t-butyl-                             N'-(3-toluoyl)hydrazine was prepared form N-                                   (4-acetylbenzoyl)-N'- .sub.- t-butyl-N'-(3-toluoyl)                            hydrazine using methyltriphenylphosphonium                                     bromide and  -n-butyl lithium as base and tetra-                               hydrofuran solvent in a Wittig reaction.                             541       N-(4-(2-hydroxyethyl)benzoyl)-N'- .sub.- t-butyl-N'-                           (3,5-dimethylbenzoyl)hydrazine was prepared                                    from N-(4-(2-acetoxyethyl)benzoyl)-N'- .sub.- t-butyl-                         N'-(3,5-dimethylbenxoyl)hydrazine using sodium                                 hydroxide as base and methanol as solvent in                                   a hydrolysis.                                                        ______________________________________                                    

By following substantially the processes for preparing the compounds of the present invention as described above and as exemplified by the illustrative preparation of the compounds of Examples 635 to 639 and 642 and using the appropriately substituted reactants, the compounds of Examples 640, 641 and 643 to 645 were prepared.

By following substantially the processes for preparing the compounds as described above and as exemplified by the illustrative preparation of the compounds of Examples 646, 648, 654, 656, 659 and 660 and using the appropriately substituted reactants, the compounds of Examples 647, 649 to 653, 655, 657, 658 and 661 to 681 were prepared.

By following substantially the procedures in processes described above as exemplified above by the preparation of the compounds of Examples 682, 683, 688, 689, 691, 699 and 702 and using the appropriately substituted reactants, the compounds of Examples 684 to 687, 690, 692 to 698, 700, 701, 703 to 721 and 991 were prepared.

By following substantially the procedures in the processes described above and as exemplified by the preparation of the compounds of Examples 722, 723, 724, 727, 729, 733, 737, 738, 739, 743, 754 and 755 and using the appropriately substituted reactants, the compounds of Examples 725, 726, 728, 730 to 732, 734 to 736, 740 to 742, 744 to 753, 756 and 992 were prepared.

By following substantially the procedures in the processes described above and as exemplifed by the preparation of the compounds of Examples 764, 765, 766, 767, 772, 778 and 787 and using the appropriately substituted reactants, the compounds of Examples 768 to 771, 773 to 777, 779 to 786 and 788 to 794 were prepared.

By following substantially the procedures in Example 802 (without catalyst) or 809 (with catalyst) and using the reactants shown below in Table XI, the products of Examples 802 to 818 were prepared.

                  TABLE XI                                                         ______________________________________                                         Ex.  Compound of   Compound of Compound of                                     No.  Formula VII   Formula VIIIa                                                                              Formula VI                                      ______________________________________                                         802  benzoylhydrazine                                                                             acetone     benzoyl                                                                        chloride                                        803  benzoylhydrazine                                                                             acetone     4-chlorobenzoyl                                                                chloride                                        804  4-toluoylhydrazine                                                                           acetone     3-methylbenzoyl                                                                chloride                                        805  benzoylhydrazine                                                                             acetone     3-methylbenzoyl                                                                chloride                                        806  4-chlorobenzoyl-                                                                             acetone     4-chlorobenzoyl                                      hydrazine                 chloride                                        807  4-toluoylhydrazine                                                                           acetone     3,5-dimethylbenzoyl                                                            chloride                                        808  4-toluoylhydrazine                                                                           acetone     4-fluorobenzoyl                                                                chloride                                        809  4-toluoylhydrazine                                                                           acetone     4-methylbenzoyl                                                                chloride                                        810  benzoylhydrazine                                                                             methyl-     benzoyl chloride                                                   ethylketone                                                 811  thienoylhydrazine                                                                            acetone     3-methylbenzoyl                                                                chloride                                        812  4-ethylbenzoyl-                                                                              acetone     3,5-dimethylbenzoyl                                  hydrazine                 chloride                                        813  2-toluoylhydrazine                                                                           acetone     3,5-dimethylbenzoyl                                                            chloride                                        814  4-chlorobenzoyl-                                                                             acetone     3-methylbenzoyl                                      hydrazine                 chloride                                        815  2,4-difluorobenzoyl-                                                                         acetone     4-chlorobenzoyl                                      hydrazine                 chloride                                        816  2-toluoylhydrazine                                                                           acetone     3-methylbenzoyl                                                                chloride                                        817  2-nitrobenzoyl-                                                                              acetone     3-methylbenzoyl                                      hydrazine                 chloride                                        818  2-chlorobenzoyl-                                                                             acetone     3-methylbenzoyl                                      hydrazine                 chloride                                        ______________________________________                                    

Examples 820 and 821 were made generally in accordance with the procedures for Example 822 above.

The (trimethylsilymethyl)hydrazine, trifluoroalkyl hydrazine and (2-carbomethoxy-2-propyl)hydrazine were made generally in accordance with the procedures from Noll, J. E.; Sprier, J. L.; Daubert, B. F.; JACS 73, 3867, 1951; Hung, S. C.; Le; Breton, G. C.; JOC 46, 5413, 1981; and Organic Synthesis Vol 5, pg. 43, respectively. From these starting materials Examples 795-801, 819 and 823-828 were made generally in accordance with the procedure for Example 822 above.

The reactant shown below in Table XII were used to prepare Examples 795-801, 819-828 and 969-978.

                  TABLE XII                                                        ______________________________________                                         Ex.  Compound of  Compound of   Compound of                                    No.  Formula III  Formula IV    Formula VI                                     ______________________________________                                         795  2,3-dimethyl (1-methyl-2,2,2-                                                                             2,4-dichloro                                        benzoylchloride                                                                             trifluorethyl)                                                                               benzoylchloride                                                  hydrazine                                                    796  2,3-dimethyl (1-methyl-2,2,2-                                                                             3,5-dimethyl                                        benzoylchloride                                                                             trifluoroethyl)                                                                              benzoylchloride                                                  hydrazine                                                    797  2-3-dimethyl (1-methyl-2,2,2-                                                                             2-nitro-5-                                          benzoylchloride                                                                             trifluoroethyl)                                                                              toluoylchloride                                                  hydrazine                                                    798  benzoylchloride                                                                             (1-methyl-2,2,2-                                                                             benzoylchloride                                                  trifluoroethyl)                                                                hydrazine                                                    799  3,4-dichloro (2,2,2-trifluoroethyl)                                                                       3,4-dichloro                                        benzoylchloride                                                                             hydrazine     benzoylchloride                                800  4-chlorobenzoyl                                                                             (2,2,2-trifluoroethyl)                                                                       4-chlorobenzoyl                                     chloride     hydrazine     chloride                                       801  benzoylchloride                                                                             (2,2,2-trifluoroethyl)                                                                       benzoylchloride                                                  hydrazine                                                    819  benzoylchloride                                                                             (1-carbmethoxy-1-                                                                            benzoylchloride                                                  methylethyl)                                                                   hydrazine                                                    820  4-toluoylchloride                                                                           (1,1-dimethyl-3-                                                                             4-toluoylchloride                                                butenyl)hydrazine                                            821  3-toluoylchloride                                                                           (1,1-dimethyl-3-                                                                             3-toluoylchloride                                                butenyl)hydrazine                                            822  benzoylchloride                                                                             (1,1-dimethyl-3-                                                                             benzoylchloride                                                  butenyl)hydrazine                                            823  4-ethylbenzoyl                                                                              (trimethylsilyl-                                                                             2-nitro-5-toluoyl                                   chloride     methyl)hydrazine                                                                             chloride                                       824  4-chlorobenzoyl                                                                             (trimethylsilyl-                                                                             4-chlorobenzoyl                                     chloride     methyl)hydrazine                                                                             chloride                                       825  2-toluoyl    (trimethylsisly-                                                                             2-toluoyl                                           chloride     methyl)hydrazine                                                                             chloride                                       826  2-nitrobenzoyl                                                                              (trimethylsilyl-                                                                             2-nitrobenzoyl                                      chloride     methyl)hydrazine                                                                             chloride                                       827  benzoyl      (trimethylsilyl-                                                                             benzoyl                                             chloride     methyl)hydrazine                                                                             chloride                                       828  4-ethylbenzoyl                                                                              (trimethylsilyl-                                                                             3,5-dimethyl                                        chloride     methyl)hydrazine                                                                             benzoylchloride                                969  4-toluoyl    (2-methyl-2-  benzoylchloride                                     chloride     propenyl)hydrazine                                           970  4-toluoyl    (2-methyl-2-  3-toluoylchloride                                   chloride     propenyl)hydrazine                                           971  benzoyl      (1,5-dimethyl-1-                                                                             2-bromobenzoyl                                      chloride     heptenyl)hydrazine                                                                           chloride                                       973  4-methylbenzoyl                                                                             (2-bromo-2,2-di-                                                                             3-toluoylchloride                                   chloride     methylethyl)                                                                   hydrazine                                                    974  4-toluoyl    (1-carbethoxyethyl)                                                                          benzoylchloride                                     chloride     hydrazine                                                    975  4-toluoyl    (1-carbethoxyethyl)                                                                          2-nitrobenzoyl                                      chloride     hydrazine     chloride                                       976  4-toluoyl    (2-dimethylamino-                                                                            3,5-dimethyl                                        chloride     1-methylethyl)                                                                               benzoylchloride                                                  hydrazine                                                    977  4-toluoyl    (2-hydroxy-2,2-                                                                              benzoylchloride                                     chloride     dimethylethyl)                                               978  4-toluoyl    (2-hydroxy-2l,2-                                                                             3,5-dimethyl                                        chloride     dimethylethyl)                                                                               benzoyolchloride                                                 hydrazine                                                    ______________________________________                                    

By following substantially the procedure in Examples 829, 837 and 853 and using the reactants shown in Table XIII, the products of Example Nos. 830-836, 838-852 and 854 were prepared.

                                      TABLE XIII                                   __________________________________________________________________________     Ex.                                                                            No.                                                                               Halide    Hydrazine  Base   Solvent                                         __________________________________________________________________________     830                                                                               4-chlorobenzyl                                                                           N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  bromide   hydrazine                                                         831                                                                               2,4-dichloro-                                                                            N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  benzyl bromide                                                                           hydrazine                                                         832                                                                               3,4-dichloro-                                                                            N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  benzyl bromide                                                                           hydrazine                                                         833                                                                               4-trifluoromethyl-                                                                       N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  benzyl bromide                                                                           hydrazine                                                         834                                                                               4-methoxycarbonyl-                                                                       N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  benzyl bromide                                                                           hydrazine                                                         835                                                                               2-nitrobenzyl                                                                            N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  bromide   hydrazine                                                         836                                                                               4-fluorobenzyl                                                                           N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  bromide   hydrazine                                                         838                                                                               2-bromobenzyl                                                                            N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  bromide   hydrazine                                                         839                                                                               2-cyanobenzyl                                                                            N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  bromide   hydrazine                                                         840                                                                               benzyl bromide                                                                           N'- .sub.- t-butyl-N-                                                                     triethylamine                                                                         dimethylformamide                                            thienoyl hydrazine                                                841                                                                               4-cyanobenzyl                                                                            N'- .sub.- t-butyl-N-(4-                                                                  triethylamine                                                                         dimethylformamide                                  bromide   methylbenzoyl)                                                                 hydrazine                                                         842                                                                               benzyl bromide                                                                           N'- .sub.- t-butyl-N-(4-                                                                  triethylamine                                                                         dimethylformamide                                            methylbenzoyl)                                                                 hydrazine                                                         843                                                                               3-nitrobenzyl                                                                            N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  bromide   hydrazine                                                         844                                                                               4-methoxybenzyl                                                                          N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  bromide   hydrazine                                                         845                                                                               3-methoxybenzyl                                                                          N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  bromide   hydrazine                                                         846                                                                               3-methylbenzyl                                                                           N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  bromide   hydrazine                                                         847                                                                               3-methylbenzyl                                                                           N'- .sub.- t-butyl-N-(4-                                                                  triethylamine                                                                         dimethylformamide                                  bromide   methylbenzoyl)                                                                 hydrazine                                                         848                                                                               4-methylbenzyl                                                                           N'- .sub.- t-butyl-N-benzoyl                                                              triethylamine                                                                         dimethylformamide                                  bromide   hydrazine                                                         849                                                                               4-methylbenzyl                                                                           N'- .sub.- t-butyl-N-(4-                                                                  triethylamine                                                                         dimethylformamide                                  bromide   methylbenzoyl)                                                                 hydrazine                                                         850                                                                               benzyl bromide                                                                           N'- .sub.- t-butyl-N-(3,4-                                                                triethylamine                                                                         dimethylformamide                                            dichlorobenzoyl)                                                               hydrazine                                                         851                                                                               4-methylbenzyl                                                                           N'- .sub.- t-butyl-N-(3,4-                                                                triethylamine                                                                         dimethylformamide                                  bromide   dichlorobenzoyl)                                                               hydrazine                                                         852                                                                               benzyl bromide                                                                           N'- .sub.- t-butyl-N-                                                                     triethylamine                                                                         dimethylformamide                                            (2-pyridinyl)                                                                  hydrazine                                                         854                                                                               2-methylbenzyl                                                                           N'- .sub.- t-butyl-N-                                                                     triethylamine                                                                         dimethylformamide                                  bromide   benzoyl hydrazine                                                 __________________________________________________________________________

By following substantially the procedures in Example 855 and using the reactants shown in Table XIV, the products of Example Nos. 856-863 were prepared.

                  TABLE XIV                                                        ______________________________________                                         Ex.                                                                            No.  Hydrazone           Base       Solvent                                    ______________________________________                                         856  N'- .sub.- t-butyl-N'-(4-fluorobenzoyl)-                                                           sodium     dry                                             benzaldehyde hydrazone                                                                             cyanobo-   methanol                                                            rohydride                                             857  N'- .sub.- t-butyl-N'-(2-bromobenzoyl)-                                                            sodium     dry                                             benzaldehyde hydrazone                                                                             cyanobo-   methanol                                                            rohydride                                             858  N'- .sub.- t-butyl-N'-(3,4-dichloro-                                                               sodium     dry                                             benzoyl) benzaldehyde                                                                              cyanobo-   methanol                                        hydrazone           rohydride                                             859  N'- .sub.- t-butyl-N'-(2-methylbenzoyl)                                                            sodium     dry                                             benzaldehyde hydrazone                                                                             cyanobo-   methanol                                                            rohydride                                             860  N'- .sub.- t-butyl-N'-(3,4-dichloro-                                                               sodium     dry                                             benzoyl)-3-methylbenzaldehyde                                                                      cyanobo-   methanol                                        hydrazone           rohydride                                             861  N'- .sub.- t-butyl-N'-benzoyl-3-methyl-                                                            sodium     dry                                             benzaldehyde hydrazone                                                                             cyanobo-   methanol                                                            rohydride                                             862  N'- .sub.- t-butyl-N'-2-thienoyl-3-                                                                sodium     dry                                             methylbenzaldehyde hydrazone                                                                       cyanobo-   methanol                                                            rohydride                                             863  N'- .sub.- t-butyl-N'-benzoyl-methyl-2-                                                            sodium     dry                                             pyridinylbenzaldehyde hydrazone                                                                    cyanobo-   methanol                                                            rohydride                                             ______________________________________                                    

By following substantially the procedures in Example 864 and using the reactants shown in Table XV, the products of Example Nos. 865-869 were prepared.

                                      TABLE XV                                     __________________________________________________________________________     Ex                                                                             No.                                                                               Benzaldehyde                                                                          Halide   Base   Solvent                                                                             Solvent System                                  __________________________________________________________________________     865                                                                               benzaldehyde                                                                          4-fluorobenzoyl                                                                         triethylamine                                                                         toluene                                                                             pyridine/methylene                                        chloride             chloride                                        866                                                                               benzaldehyde                                                                          3,4-dichloro-                                                                           triethylamine                                                                         toluene                                                                             pyridine/methylene                                        benzoyl chloride     chloride                                        867                                                                               benzaldehyde                                                                          2-bromobenzoyl                                                                          triethylamine                                                                         toluene                                                                             pyridine/methylene                                        chloride             chloride                                        868                                                                               3-methyl-                                                                             benzoyl  triethylamine                                                                         toluene                                                                             pyridine-methylene                                 benzaldehyde                                                                          chloride             chloride                                        869                                                                               benzaldehyde                                                                          2-thienoyl                                                                              triethylamine                                                                         toluene                                                                             pyridine/methylene                                        chloride             chloride                                        __________________________________________________________________________

Example No. 874 was prepared by following substantially the procedures in Example 873 and using N'-t-butyl-N'-benzoylhydrazine, 3-methylbenzoyl formic acid, methanesulfonyl chloride in toluene and saturated sodium bicarbonate.

By following substantially the procedures in Example 878 and using the hydrazine shown in Table XVI and the reactants in Example 878, the products of Example Nos. 875-877 were prepared.

                  TABLE XVI                                                        ______________________________________                                         Ex. No.      Hydrazine                                                         ______________________________________                                         875          N'- .sub.- t-butyl-N-(2,3-dimethylbenzoyl)                                     hydrazine                                                         876          N'- .sub.- t-butyl-N-(4-methylbenzoyl)                                         hydrazine                                                         877          N'- .sub.- t-butyl-N-(4-ethylbenzoyl) hydrazine                   ______________________________________                                    

By following substantially the procedure in Example Nos. 882 and 883 and using the reactants shown in Table XVII, the products of Example Nos. 879-881 and 884-886, were prepared.

                                      TABLE XVII                                   __________________________________________________________________________     Ex.                                                                            No.                                                                               Hydrazine                                                                               Base      Solvent                                                                             Halide                                              __________________________________________________________________________     879                                                                               N'- .sub.- t-butyl-N-                                                                   sodium hydroxide                                                                         toluene                                                                             alpha-isopropyl-4-                                     (2,3-dimethyl-          chlorophenylacetyl                                     benzoyl)hydrazine       chloride                                            881                                                                               N'- .sub.- t-butyl-N-                                                                   sodium hydroxide                                                                         toluene                                                                             phenylacetyl chloride                                  (4-chlorobenzoyl)                                                              hydrazine                                                                   884                                                                               N'- .sub.- t-butyl-N-                                                                   sodium bicarbonate                                                                       toluene                                                                             alpha-chlorophenyl-                                    (4-chlorobenzoyl)       acetyl chloride                                        hydrazine                                                                   885                                                                               N'- .sub.- t-butyl-N-                                                                   sodium hydroxide                                                                         toluene                                                                             phenylacetyl chloride                                  (2,3-dimethyl-                                                                 benzoyl)                                                                       hydrazine                                                                   886                                                                               N'- .sub.- t-butyl-N-                                                                   sodium hydroxide                                                                         toluene                                                                             phenylacetyl chloride                                  (4-ethylbenzoyl)                                                               hydrazine                                                                   __________________________________________________________________________     Ex.                                                                            No.     Hydrazine         Halide                                               __________________________________________________________________________     902     N'- .sub.- t-butyl-N-2,3-dimethylbenzoyl-                                                        methacryloyl                                                 N'-3-methylbenzoyl hydrazine                                                                     chloride                                             903     N'- .sub.- t-butyl-N-2,3-dimethylbenzoyl-                                                        2-furoyl chloride                                            N'-3-methylbenzoyl hydrazine                                           907     N'- .sub.- t-butyl-N-4-ethylbenzoyl-N'-                                                          acryloyl chloride                                            2,3-dimethylbenzoyl hydrazine                                          908     N,N'-benzoyl-N'- .sub.- t-butyl hydrazine                                                        acryloyl chloride                                    909     N,N'-benzoyl-N'- .sub.- t-butyl hydrazine                                                        4-ethylbenzoyl                                                                 chloride                                             910     N,N'-benzoyl-N'- .sub.- t-butyl hydrazine                                                        4-pentenoyl                                                                    chloride                                             911     N,N'-benzoyl-N'- .sub.- t-butyl hydrazine                                                        tigloyl chloride                                     912     N'- .sub.- t-butyl-N-benzoyl-N'-                                                                 acetyl chloride                                              2,4-dichlorobenzoyl hydrazine                                          913     N'- .sub.- t-butyl-N-benzoyl-N'-                                                                 methacryloyl                                                 2,4-dichlorobenzoyl hydrazine                                                                    chloride                                             __________________________________________________________________________

Example Nos. 904 and 906 were prepared by following substantially the procedures in Example 905 and using N'-t-butyl-N-(2,3-diemthylbenzoyl) hdyrazine and ethanol, and N'-t-butyl-N-benzoylhydrazine and methanol, respectively.

Example Nos. 915 and 916 were prepared by following substantially the procedures in Example 914 and using 4-methylbenzene sulfonyl and 4-fluorobenzene sulfonyl, respectively.

By following substantially the procedure in Example 893 and using the hydrazine and halide shown in Table XVIII and the other reactants in Example 893, the products of Example Nos. 887-892, 894-903 and 907-913 were prepared.

                  TABLE XVIII                                                      ______________________________________                                         Ex.                                                                            No.  Hydrazine            Halide                                               ______________________________________                                         887  N,N'-benzoyl-N'- .sub.- t-butyl hydrazine                                                           acetyl chloride                                      888  N,N'-benzoyl-N'- .sub.- t-butyl hydrazine                                                           methylchloroformate                                  889  N,N'-benzoyl-N'- .sub.- t-butyl hydrazine                                                           methoxyacetyl                                                                  chloride                                             890  N,N'-benzoyl-N'- .sub.- t-butyl hydrazine                                                           vinyl chloroformate                                  891  N,N'-benzoyl-N'- .sub.- t-butyl hydrazine                                                           crotonyl chloride                                    892  N,N'-benzoyl-N'- .sub.- t-butyl hydrazine                                                           tigloyl chloride                                     894  N'- .sub.- t-butyl-N-4-ethylbenzoyl-N'-                                                             methylacryloyl                                            3,5-dimethylbenzoyl hydrazine                                                                       chloride                                             895  N'- .sub.- t-butyl-N-4-ethylbenzoyl-N'-                                                             acetyl chloride                                           3,5-dimethylbenzoyl hydrazine                                             896  N'- .sub.- t-butyl-N-4-ethylbenzoyl-N'-                                                             methylchloroformate                                       3,5-dimethylbenzoyl hydrazine                                             897  N'- .sub.- t-butyl-N-4-ethylbenzoyl-N'-                                                             methoxyacetyl                                             3,5-dimethylbenzoyl hydrazine                                                                       chloride                                             898  N'- .sub.- t-butyl-N-4-ethylbenzoyl-N'-                                                             vinyl chloroformate                                       3,5-dimethylbenzoyl hydrazine                                             899  N'- .sub.- t-butyl-N-4-ethylbenzoyl-N'-                                                             2-furoyl chloride                                         3,5-dimethylbenzoyl hydrazine                                             900  N'- .sub.- t-butyl-N-4-ethylbenzoyl-N' -                                                            propionyl chloride                                        3,5-dimethylbenzoyl hydrazine                                             901  N'- .sub.- t-butyl-N-2,3-dimethylbenzoyl-                                                           acetyl chloride                                           N'-3-methylbenzoyl hydrazine                                              ______________________________________                                    

Example Nos. 917 and 919-921 were prepared by following substantially the procedures in Example 918 except using the hydrazine and halide shown in Table XIX.

                  TABLE XIX                                                        ______________________________________                                         Ex.                                                                            No.     Hydrazine           Halide                                             ______________________________________                                         917     N'- .sub.- t-butyl-N-benzoyl hydrazine                                                             4-fluorobenzene                                                                sulfonyl chloride                                  919     N'- .sub.- t-butyl-N-benzoyl hydrazine                                                             4-methylbenzene                                                                sulfonyl chloride                                  920     N'- .sub.- t-butyl-N-(2-pyridinoyl)                                                                benzene sulfonyl                                           hydrazine           chloride                                           921     N'- .sub.- t-butyl-N-benzoyl hydrazine                                                             2-thienyl                                                                      sulfonyl chloride                                  ______________________________________                                    

Example No. 1014 was prepared by following substantially the procedure in Example 1013 and using mucobromic acid.

Example Nos. 999 to 1007 and 1012 were prepared by following substantially the procedure of Example 872 and using the appropriately substituted reactants.

Example Nos. 1009 to 1011 were prepared by following substantially the procedure of Example 1008 and using the appropriately substituted reactants.

It will be appreciated by those skilled in the art that compounds of Formula I can be used as precursors for preparing other compounds of Formula I by procedures well known to those skilled in the art. For example, a suitable compound of Formula I can be reduced, alkylated, substituted, esterified, hydrolyzed or the like.

As previously noted, the compounds of the present invention exhibit excellent insecticidal activity and are most active against insects of the orders Lepidoptera and Coleoptera.

In general, for the control of insects in agriculture, horticulture and forestry, the compounds of the present invention may be used at a dosage corresponding to from about 10 grams to about 10 kilograms of the active substance per hectare and from about 100 grams to about 5 kilograms per hectare of the active substance is preferred. The exact amount of dosage for a given situation can be routinely determined and depends on a variety of factors, for example, the substance used, the kind of insect, the formulation used, the state of the crop infested with the insect and the prevailing weather conditions. The term "insecticidal" as employed in the specification and claims of this application is to be construed as any means which adversely affects the existence or growth of the target insects at any stage in their life cycle. Such means can comprise a complete killing action, eradication, arresting in growth, inhibition, reducing in number, reproductive inhibition (such as ovicidal or chemisterilant) or any combination thereof. The term "control" as employed in the specification and claims of this application is to be construed as meaning "insecticidal" or protecting plants from insect damage. By "insecticidally effective amount" is meant that dosage of active substance sufficient to exert insect "control."

The compounds of the present invention, for practical applications, can be utilized in the form of compositions or formulations. Examples of the preparation of compositions and formulations can be found in the American Chemical Society publication "Pesticidal Formulation Research," (1969), Advances in Chemistry Series No. 86, written by Wade Van Valkenburg; and the Marcel Dekker, Inc. publication "Pesticide Formulations," (1973), edited by Wade Van Valkenburg. In these compositions and formulations, the active substance or substances are mixed with conventional inert agronomically acceptable (i.e., plant compatible and/or pesticidally inert) diluents or extenders such as solid carrier material or liquid carrier material, of the type usable in conventional compositions or formulations. By agronomically acceptable carrier is meant any substance which can be used to dissolve, disperse or diffuse the active ingredient in the composition without impairing the active ingredient's effectiveness and which by itself has no significant detrimental effect on the soil, equipment, desirable plants or agronomic environment. If desired, conventional adjuvants such as surfactants, stabilizers, antifoam agents and antidrift agents may also be added.

Examples of compositions and formulations according to the invention are aqueous solutions and dispersions, oily solutions and oil dispersions, pastes, dusting powders, wettable powders, emulsifiable concentrates, flowables, granules, baits, invert emulsions, aerosol compositions and fumigating candles.

Wettable powders, pastes, flowables and emulsifiable concentrates are concentrated preparations which are diluted with water before or during use.

Baits are preparations generally comprising a food or other substance attractive to the target pest, that includes at least one lethal or non-lethal toxicant. Lethal toxicants kill the pest upon ingesting the bait while non-lethal toxicants change the behavior, feeding habits and physiology of the pest for the purpose of control.

The invert emulsions are mainly used for air application, where large areas are treated with a comparatively small amount of preparation. The invert emulsion may be prepared in the spraying apparatus shortly before, or even during, the spraying operation by emulsifying water in an oil solution or an oil dispersion of the active substance.

Compositions and formulations are prepared in a known manner, for instance by extending the active compounds with conventional dispersible liquid diluent carriers and/or dispersible solid carriers optionally with the use of carrier vehicle assistants, e.g., conventional surface-active agents, including emulsifying agents and/or dispersing agents, whereby, for example, in the case where water is used as diluent, organic solvents may be added as auxiliary solvents. The following may be chiefly considered for use as conventional carrier vehicles for this purpose: aerosol propellants which are gaseous at normal temperatures and pressures, such as halogenated hydrocarbons, e.g., dichlorodifluoromethane and trifluorochloromethane, as well as butane, propane, nitrogen and carbon dioxide; inert dispersible liquid diluent carriers, including inert organic solvents, such as aromatic hydrocarbons (e.g., benzene, toluene, xylene, alkyl naphthalenes, etc.), halogenated, especially chlorinated, aromatic hydrocarbons (e.g., chlorobenzenes, etc.), cycloalkanes (e.g., cyclohexane, etc.), paraffins (e.g., petroleum or mineral oil fractions), chlorinated aliphatic hydrocarbons (e.g., methylene chloride, chloroethylenes, etc.), vegetable oils (e.g., soybean oil, cottonseed oil, corn oil, etc.), alcohols (e.g., methanol, ethanol, propanol, butanol, glycol, etc.) as well as ethers and esters thereof (e.g., glycol monomethyl ether, etc.), amines (e.g., ethanolamine, etc.), amides (e.g., dimethyl formamide, etc.), sulfoxides (e.g., dimethyl sulfoxide, etc.), acetonitrile, ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, isophorone, etc.), and/or water; solid carriers including ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates; solid carriers for granules include crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. The following may be chiefly considered for use as conventional carrier vehicle assistants: emulsifying agents, such as cationic and/or nonionic and/or anionic emulsifying agents (e.g., polyethylene oxide esters of fatty acids, polyethylene oxide ethers of fatty alcohols, alkyl sulfates, alkyl sulfonates, aryl sulfonates, albumin hydrolysates, etc., and especially alkyl arylpolyglycol ethers, magnesium stearate, sodium oleate, etc.); and/or dispersing agents, such as lignin, sulfite waste liquors, methyl cellulose, etc.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.

If desired, it is possible to use colorants in compositions and formulations containing compounds of the present invention such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The active compounds of the present invention may be employed alone or in the form of mixtures with one another and/or with such solid and/or liquid dispersible carrier vehicles and/or with other known compatible active agents, especially plant protection agents, such as other insecticides, arthropodicides, nematicides, fungicides, bactericides, rodenticides, herbicides, fertilizers, growth-regulating agents, synergists, etc., if desired, or in the form of particular dosage preparations for specific application made therefrom, such as solutions, emulsions, suspensions, powders, pastes, and granules which are thus ready for use.

As concerns commercially marketed preparations, these generally contemplate carrier composition mixtures in which the active compound is present in an amount substantially between about 0.1% and 99% by weight, and preferably between about 1% and 75% by weight, of the mixture. Carrier composition mixtures suitable for direct application or field application generally contemplate those in which the active compound is used in an amount substantially between about 0.0001% and 5%, preferably between about 0.001% and 3%, by weight of the mixture. Thus the present invention contemplates overall formulations and compositions which comprise mixtures of a conventional dispersible carrier such as (1) a dispersible inert finely divided carrier solid, and/or (2) a dispersible carrier liquid such as an inert organic solvent and/or water, preferably including a surface-active effective amount of a carrier vehicle assistant (e.g., a surface-active agent, such as an emulsifying agent and/or a dispersing agent), and an amount of the active compound generally, between about 0.0001% and about 99% by weight of the composition, preferably between about 0.001% and about 90% by weight of the composition, and more preferably between about 0.01% and about 75% by weight of the composition, which is effective for the purpose in question.

The active compounds can be applied as sprays by methods commonly employed, such as conventional high-gallonage hydraulic sprays, low gallonage sprays, ultra-low-volume sprays, airblast spray, aerial sprays, and dusts. If low volume applications are desired, a solution of the compound is usually used. In ultra-low-volume applications, a liquid composition containing the active compound is usually applied as a spray (e.g., mist) by means of atomizing equipment in finely divided form (average particle size of from about 50 to about 100 microns or less) using airplane crop spraying techniques. Typically only a few liters per hectare are needed and often amounts up to about 15 to 1000 g/hectare, preferably about 40 to 600 g/hectare are sufficient. With ultra-low-volume, it is possible to use highly concentrated liquid compositions with said liquid carrier vehicles containing from about 20 to about 95% by weight of the active compound.

Furthermore, the present invention contemplates methods of killing, combatting or controlling insects, which comprises contacting insects with a correspondingly combative or toxic amount (i.e., an insecticidally effective amount) of at least one active compound of the invention alone or together with a carrier vehicle (composition or formulation) as noted above. The term "contacting" as employed in the specification and claims of this application is to be construed as applying to at least one of (a) such insects and (b) the corresponding habitat thereof (i.e., the locus to be protected, for example, to a growing crop or to an area where a crop is to be grown) the active compound of this invention alone or as a constituent of a composition or formulation. The instant formulations or compositions are applied in the usual manner, for instance by spraying, atomizing, vaporizing, scattering, dusting, watering, squirting, sprinkling, pouring, fumigating, dry dressing, moist dressing, wet dressing, slurry dressing, encrusting and the like.

It will be realized, of course, that the concentration of the particular active compound utilized in admixture with the carrier vehicle will depend upon such factors as the type of equipment employed, method of application, area to be treated, types of pests to be controlled and degree of infestation. Therefore, in special cases it is possible to go above or below the aforementioned concentration ranges.

Granular preparations are produced for example, by taking up the active substance in a solvent and by using the resulting solution, as the case may be in the presence of a binder, to impregnate a granular carrier material, such as porous granules (for example, pumice and attaclay), or chopped tobacco stems or the like.

A granular preparation (frequently termed a "pellet") may alternatively be produced by compressing the active substance together with powdered minerals in the presence of lubricants and binders and by disintegrating and straining the composite to the desired grain size.

Dusts are obtainable by intimately mixing the active substance with an inert solid carrier material in a concentration of from about 1 to about 50% by weight. Examples of suitable solid carrier materials are talc, kaolin, pipe clay, diatomaceous earth, dolomite, gypsum, chalk, bentonite, attapulgite and colloidal Si02 or mixtures of these and similar substances. Alternatively organic carrier materials such as, for example, ground walnut shells may be used.

Wettable powders and flowables are produced by mixing from about 10 to about 99 parts by weight of a solid inert carrier such, for example, as the aforementioned carrier materials with from about 1 to about 80 parts by weight of the active substance optionally dissolved in a volatile solvent such as acetone, from about 1 to about 5 parts by weight of a dispersing agent such, for example, as the lignosulfonates or alkylnaphthalene sulfonates known for this purpose and preferably also from about 0.5 to about 5 parts by weight of a wetting agent, such as fatty alcohol sulfates, or alkylarylsulfonates of fatty acid condensation products. In the case of flowables, a liquid inert carrier such as water is also included.

To produce emulsifiable concentrates the active compound is dissolved or finely divided in a suitable solvent which preferably is poorly miscible with water, an emulsifier being added to the resulting solution. Examples of suitable solvents are xylene, toluene, high-boiling aromatic petroleum distillates, for example solvent naphtha, distilled tar oil and mixtures of these liquids. Examples of suitable emulsifiers are alkylphenoxypolyglycol ethers, polyoxyethylene sorbitan esters of fatty acids or polyoxyethylene sorbitol esters of fatty acids. The concentration of the active compound in these emulsifiable concentrates is not restricted within narrow limits and may vary between about 2% and about 50% by weight depending upon toxicant solubility. A suitable liquid highly concentrated primary composition other than an emulsifiable concentrate is a solution of the active substance in a liquid which is readily miscible with water, for example, acetone, to which solution a dispersant and, as the case may be, a wetting agent are added. When such a primary composition is diluted with water shortly before or during the spraying operation an aqueous dispersion of the active substance is obtained.

An aerosol preparation according to the invention is obtained in the usual manner by incorporating the active substance or a solution thereof in a suitable solvent in a volatile liquid suitable for use as a propellant such, for example, as a mixture of chlorine and fluorine derivatives of methane and ethane.

Fumigating candles or fumigating powders, i.e., preparations which when burning are capable of emitting a pesticidal smoke, are obtained by taking up the active substance in a combustible mixture which may, for example, comprise a sugar or a wood, preferably in the ground form, as a fuel, a substance to sustain combustion such, for example, as ammonium nitrate or potassium chlorate, and furthermore a substance for retarding combustion, for example kaolin, bentonite and/or colloidal silicic acid.

A bait preparation comprises a food or other substance attractive to pests, a carrier, the toxicant and may optionally include other substances commonly used in preparations of this kind, such as, a preservative to inhibit bacterial and fungal growth, a waterproofing agent to prevent disintegration under wet conditions and dyes or colorants as described above.

In addition to the aforementioned ingredients, the preparations according to the invention may also contain other substances commonly used in preparations of this kind.

For example, a lubricant, such as calcium stearate or magnesium stearate, may be added to a wettable powder or to a mixture to be granulated. Furthermore, there may, for example, be added "adhesives" such as polyvinylalcohol cellulose derivatives or other colloidal materials, such as casein, to improve the adherence of this pesticide to the surface to be protected.

Representative preparation of compositions and formulations including the compounds of the present invention are set forth below as Examples A through I by way of illustration but not limitation.

    ______________________________________                                         Example A                                                                      Granular                                                                       Ingredient            %/wt.                                                    ______________________________________                                         Toxicant and toxicant impurities                                                                     0.25                                                     Triton ® X-305 (binder)                                                                          0.25                                                     (Octylphenyl-30-ethylene                                                       oxide ethanol)                                                                 Agsorb ® 24/48 (diluent)                                                                         99.50                                                    (Montmorillonite clay)                                                         ______________________________________                                    

Preparation: The toxicant and Triton® X-305 are dissolved into methylene chloride and the mixture is added to the Agsorb® with continuous mixing. The methylene chloride is then allowed to evaporate.

    ______________________________________                                         Example B                                                                      Dust                                                                           Ingredient            %/wt.                                                    ______________________________________                                         Toxicant and toxicant impurities                                                                     1.0                                                      Talc                  99.0                                                     ______________________________________                                    

Preparation: Toxicant is dissolved in excess acetone and the mixture is impregnated onto the talc. The acetone is then permitted to evaporate.

    ______________________________________                                         Example C                                                                      Wettable Powder                                                                Ingredient            %/wt.                                                    ______________________________________                                         Toxicant and toxicant impurities                                                                     31.3                                                     Duponal ® WA Dry (wetter)                                                                        2.0                                                      (Sodium lauryl sulfate)                                                        Reax ® 45A (dispersant)                                                                          5.0                                                      (Sodium lignin sulfonate)                                                      Barden clay (diluent) 31.7                                                     HiSil ® 233 (diluent)                                                                            30.0                                                     (Sodium silica)                                                                ______________________________________                                    

Preparation: The toxicant, optionally dissolved in a volatile solvent, is absorbed onto the Barden clay and HiSil® carriers The Duponal® and Reax® are then added and the entire dry mixture blended until homogeneous. The composition is then micronized to a fine particle size.

    ______________________________________                                         Example D                                                                      Emulsifiable Concentrate                                                       Ingredient             %/wt.                                                   ______________________________________                                         Toxicant and toxicant impurities                                                                      15.0                                                    Sponto ® 232T (emulsifier)                                                                        6.0                                                     (Anionic and nonionic blend of the                                             following surfactants: calcium                                                 dodecyl benzene sulfonate; and                                                 ethoxylated alkylphenol)                                                       Sponto ® 234T (emulsifier)                                                                        4.0                                                     (Anionic and nonionic blend of the                                             following surfactants: calcium                                                 dodecyl benzene sulfonate; and                                                 ethoxylated alkylphenol)                                                       Cyclohexanone (solvent)                                                                               22.5                                                    Tenneco ® 500-100 (solvent)                                                                       52.5                                                    (Aromatic solvent mixture                                                      principally comprising xylene,                                                 cumene and ethyl benzene having                                                a boiling point range of 290-345° F.)                                   ______________________________________                                    

Preparation: All ingredients are mixed together with continuous agitation until a homogeneous clear solution is obtained.

    ______________________________________                                         Example E                                                                      Aerosol                                                                        Ingredient            %/wt.                                                    ______________________________________                                         Toxicant and toxicant impurities                                                                     0.5                                                      Freon 12              99.5                                                     ______________________________________                                    

Preparation: The components are mixed and packaged under pressure in a suitable container equipped with a release spray valve.

    ______________________________________                                         Example F                                                                      Fumigating Candle or Fumigating Powder                                         Ingredient            %/wt.                                                    ______________________________________                                         Toxicant and toxicant impurities                                                                     1.0                                                      Wood dust             96.0                                                     Starch                3.0                                                      ______________________________________                                    

Preparation: Toxicant, wood dust, and starch are blended together and then molded into a candle using a small amount of water to activate the starch.

                  Example G                                                        ______________________________________                                         Bait                                                                           Method A                                                                       Ingredient            %/wt.                                                    ______________________________________                                         Toxicant and toxicant impurities                                                                     1.00                                                     Wheat Bran (carrier and attractant)                                                                  89.95                                                    Corn Syrup (attractant)                                                                              7.00                                                     Corn Oil (attractant) 2.00                                                     Kathon .sup.® 4200 (preservative)                                                                0.05                                                     (2- -n-octyl-4-isothiazolin-3-one)                                             ______________________________________                                    

Preparation: The corn oil and corn syrup are added to the wheat bran with adequate mixing. The toxicant and Kathon® are premixed with excess acetone and this solution is added to the wheat bran base with continued mixing. The acetone is then permitted to evaporate.

    ______________________________________                                         Method B                                                                       Ingredient              %/wt.                                                  ______________________________________                                         Toxicant and toxicant impurities                                                                       0.06                                                   Granulated Sugar (carrier and attractant)                                                              99.94                                                  ______________________________________                                    

EXAMPLE H Pellet

Same as Example G, Method A, with this addition: the bait composition is formed into 1/4" diameter by 3/8" long pellets using a suitable die and press apparatus.

                  Example I                                                        ______________________________________                                         Flowable                                                                       Ingredient            %/wt.                                                    ______________________________________                                         Toxicant and toxicant impurities                                                                     31.3                                                     Duponal .sup.® WA Dry (wetter)                                                                   2.0                                                      (Sodium lauryl sulfate)                                                        Reax .sup.® 45A (dispersant)                                                                     5.0                                                      (Sodium lignin sulfonate)                                                      HiSil .sup.® 233 (diluent)                                                                       30.0                                                     (Sodium silica)                                                                Kelzan .sup.® (thickener)                                                                        0.5                                                      (Xanthan gum)                                                                  Water                 31.2                                                     ______________________________________                                    

Preparation: The toxicant is absorbed onto the HiSil® carrier. The Duponal® and Reax® are then added and the entire dry mixture blended until homogeneous. The composition is then micronized to a fine particle size. The resulting powder is suspended in water and the Lekzan® added.

Compositions and formulations according to the present invention may also include known pesticidal compounds. This expands the spectrum of activity of the preparations and may give rise to synergism.

The following known insecticidal, fungicidal and acaricidal compounds are suitable for use in such a combined preparation.

Insecticides such as:

Chlorinated hydrocarbons, for example, 2,2-bis(p-chlorophenyl)-1,1,1-trichloroethane and hexachloroepoxyoctahydrodimethanonaphthalene;

Carbamates, for example, N-methyl-1-naphthylcarbamate;

Dinitrophenols, for example, 2-methyl-4,6-dinitrophenol and 2-(2-butyl)-4,6-dinitrophenyl-3,3-dimethylacrylate;

Organic phosphorus compounds, such as dimethyl-2-methoxy-3-carbonyl-1-methylvinyl phosphate, O,O-diethyl-O-p-nitrophenylphosphorothioate; N-monomethylamide of O,O-dimethyldithiophosphorylacetic acid;

Diphenylsulfides, for example, p-chlorobenzyl or p-chlorophenyl sulfide and 2,4,4',5-tetrachlorodiphenylsulfide;

Diphenylsulfonates, for example, p-chlorophenylbenzenesulfonate;

Methylcarbinols, for example, 4,4-dichloro-1-trichloromethylbenzhydrol;

Quinoxaline compounds, such as methylquinoxaline dithiocarbonate;

Amidines such as N'-(4-chloro-2-methylphenyl) N,N-dimethylformamidine;

Pyrethroids such as Allethrin;

Biologicals such as Bacillus thuringiensis preparations;

Organic tin compounds such as tricyclohexyltin hydroxide;

Synergists such as piperonyl butoxide;

Insect growth regulators such as N-benzoyl-phenyl ureas, for example, diflubenzuron.

Fungicides such as:

Organic mercury compounds, for example, phenylmercuryacetate and methylmercurycyanoguanide;

Organic tin compounds, for example, triphenyltin hydroxide and triphenyltin acetate;

Alkylenebisdithiocarbamates, for example, zinc ethylenebisthiocarbamate and manganese ethylenebisdithiocarbamate; and

2,4-dinitro-6-(2-octyl-phenylcrotonate), 1-bis(dimethylamino)phosphoryl-3-phenyl-5-amino-1,2,4-triazole, 6-methylquinoxaline-2,3-dithiocarbonate, 1,4-dithioanthraquinone-2,3-dicarbonitrile, N-trichloromethylthiophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide, N-dichlorofluoromethylthio-N-phenyl-N'-dimethylsulfonyldiamide and tetrachloroisophthalonitrile.

BIOLOGICAL ACTIVITY

It has been found by biological evaluation that compounds according to the present invention have pesticidal activity and are capable of controlling larvae and adult forms of pests, especially insects from the orders Lepidoptera and Coleoptera and most especially insects from the order Lepidoptera. One skilled in the art will know how to determine the activity of a given compound against a given insect and the dosage required to obtain general or selective insecticidal effects. The compounds of the present invention in part affect the normal development of insects, particularly insects from the order Lepidoptera, by directly and/or indirectly influencing the moulting process.

As previously noted, the compounds of the present invention are particularly suitable for controlling plant destructive insects in crops of cultivated plants, such as, but not limited to, cotton, vegetables, corn and other cereals and the like; forestry, such as, but not limited to, birch, spruce, pine, fir and the like; and ornamental plants, flowers and trees. Compounds of the present invention are also particularly suitable for controlling insects destructive to stored commodities such as seeds and the like; fruit crops, such as, but not limited to fruit and/or citrus trees, raspberry bushes and the like; and turf, such as, but not limited to, lawns, sod and the like.

In evaluating the pesticidal activity of the compounds of this invention, the following test procedures were employed.

Unless a different application rate is indicated in Table XX, a test solution containing 600 parts per million (ppm) was made by dissolving the test compound in a solvent (acetone:methanol, 1:1), adding water to give an acetone:methanol:water system of 5:5:90 and then a surfactant. A 1:1 mixture of an alkylarylpolyetheralcohol (sold under the trademark Triton® X-155) and a modified phthalic glycerol alkyl resin (sold under the trademark Triton® B-1956) was utilized at the equivalent of 1 ounce per 100 gal. of test solution as a surfactant.

Initial evaluations were made on one or more of the following pests:

    ______________________________________                                         Code                                                                           Symbol  Common Name    Latin Name                                              ______________________________________                                         SAW     Southern Armyworm                                                                             Spodoptera eridania                                     MBB     Mexican Bean Beetle                                                                           Epilachna varivestis                                    BW      Boll Weevil    Anthonomus grandis grandis                              ______________________________________                                    

For the foliar bean beetle and armyworm tests, individual bean (Phaseolus limensis var. Woods' Prolific) leaves are placed on moistened pieces of filter paper in Petri dishes. The leaves are then sprayed with the test solution using a rotating turntable and allowed to dry. The dishes are infested with 10 third instar larvae of Southern armyworm or Mexican bean beetle. The dishes are then covered.

For the Boll Weevil test ten adult weevils are placed in a 0.5 pint glass Mason jar containing a small cube of apple. The weevils are confined to the jars by fiberglass screen mesh secured by a screw-type rim cap. The jars are then sprayed with the test solution using a rotating turntable, directing the spray through the mesh into the jar.

The rotating turntable consists of a fixed, continuously operating spray nozzle under which targets are rotated at a fixed speed and distance. If the target is a Petri dish (such as for the armyworm), the distance from the nozzle is 15 inches. If the target is a Mason jar, the distance between the screened lid and the nozzle is 6 inches (10 inches from the base of the jar to the nozzle). The nozzle is located 8 inches from the rotating shaft. The targets on individual platforms revolve around the shaft at 1 revolution per 20 seconds but only a brief portion of this time occurs in the spray path. Targets pass only once under the nozzle and then are removed to drying hoods.

The nozzle used is a 1/4 JCO Spraying Systems (Wheaton, Ill.) air atomizing nozzle equipped with a No. 2850 fluid cap and No. 70 air cap. At the 10 psig air pressure used and with liquid siphon feed 0.5 GPH (gallons per hour) are delivered in a round spray pattern with a 21° spray angle. Targets are misted with spray droplets to the point that the droplets coalesce to form a uniform thin film insufficient to drown test organisms.

All treatments are maintained at 75-80° F. under continuous fluorescent light in a well-ventilated room.

For soil treatment (systemic) trials, a portion of the 600 ppm test solution is diluted to 150 ppm. Ten (10) ml of the 150 ppm test solution is pipetted into soil (approximately 200 g of standard greenhouse soil) in a 3-inch pot containing a lima bean seedling. This results in a soil concentration of approximately 8 ppm. Treated plants are maintained under existing greenhouse conditions for one week. Two bean leaves are removed and placed individually on moist filter paper in Petri dishes. One leaf is infested with 10 third instar larvae of Mexican bean beetle. The other leaf is infested with 10 third instar larvae of Southern armyworm. The dishes are then covered and held for 3 days at which time the percent control (mortality) is determined. A second observation may be made 6 days after infesting the dishes if the experimenter feels the effect may not be complete or moribund insects appear to evidence signs of some recovery. Where necessary, untreated bean leaves are introduced into dishes held for a second observation to preclude insect starvation.

The results of the initial insecticidal evaluations are given in Table XX.

Armyworm and bean beetle spray (foliar) results are 96 hour observations unless otherwise noted. Boll weevil spray results are 48 hour observations unless, in the discretion of the experimenter, particular evaluations were held for 96 hour observations if it is believed the effect of a test compound may not be complete or moribund insects appear to evidence some signs of recovery. If, after 96 hours, there was a change in the percent control, it is shown in parentheses. Soil treatment results are 72 hour observations. At the discretion of the experimenter, particular evaluations were held for 144 hour observations. If, after 144 hours, there was a change in the percent control, it is shown in parentheses. Evaluations are based on a scale of 0-100 percent in which 0 equals no activity and 100 equals total kill.

                  TABLE XX                                                         ______________________________________                                         Initial Biological Evaluations                                                        Foliar Application                                                                             Soil Application                                               Test Species    Test Species                                            Example No.                                                                             SAW      MBB     BW     MBB    SAW                                    ______________________________________                                          1       100.sup.a                                                                                0       0      80     0                                      2       100       0       0      20     0                                      3       100       60.sup.a                                                                               0     100    100                                     4       100       0       0      60     0                                      5       100       0       0      50     0                                      6        40       0       0     .sup. --.sup.b                                                                         --                                     7       100       0       0      50     0                                      8        10       0       0      --     --                                     9       100       0       0      70    100                                     10      100       0       0      60     0                                      11      100       0       0      20    100                                     12       20.sup.d                                                                               100      0      50     0                                      13      100       0       0      20    100                                     14       20.sup.d                                                                                0.sup.d                                                                                60.sup.d                                                                              0.sup.d                                                                               0.sup.d                                15      100       0       0      20     0                                      16      100       0       0      30    100                                     17      100       0       0      40    100                                     18      100      100      0     100    100                                     19      100       0      100     20     0                                      20      100       0       0      --     --                                     21      100       0       0      --     --                                     22      100       0       0      40    100                                     23      100       0      100     --     --                                     24      100       0       80     --     --                                     25      100       0       0      --     --                                     26      100      100      0      0     100                                     27      100.sup.d                                                                                0.sup.d                                                                                20.sup.d                                                                              20(40).sup.d                                                                          70.sup.d                               28       10       0       0      --     --                                     29      100       0       0      0      40                                     30      100       0       0      0      10                                     31      100      100      0       40   100                                     32       0.sup.d  20.sup.a,c                                                                             20.sup.c                                                                              --     --                                     33      100       40      0      20     0                                      34      100       20      0      70    100                                     35      100      100      0     100    100                                     36      100      100      20     90    100                                     37      100       0       0      --     --                                     38      100       90      20     0(60) 100                                     39      100       0       0      0      20                                     40       40       20      20     0      0                                      41      100       0       20     20    100                                     42      100      100      0     100    100                                     43      100      100      0     100    100                                     44      100       10      0      0(20)  0                                      45      100       0       0      0(40)  0(40)                                  46      100       0       60     40(80)                                                                                60(80)                                 47      100      100      0      80(90)                                                                               100                                     48      100      100      0(40)  40(60)                                                                               100                                     49      100      100      40(80)                                                                                10(60)                                                                               100                                     50      100       0       40(80)                                                                                40(70)                                                                                0(10)                                  51      100      100      0      70(100)                                                                               30                                     52      100      100      0      20(30)                                                                                20(50)                                 53      100       0       40     20(60)                                                                               100                                     54      100       20      0      0      0                                      55      100       10      0      0      0                                      56      100      100      0      60(80)                                                                               100                                     57      100       0       0      40(60)                                                                                0                                      58      100       20      0      20     0                                      59      100       70      20     20    100                                     60      100       40      0      0      0                                      61       80.sup.d                                                                                0       0      60(80)                                                                                0                                      62      100       40      0      20    100                                     63      100       10      0      20     0                                      64      100       20      0      0(100)                                                                                10(50)                                 65      100       20      0      0(40) 100                                     66      100       70      0      40(80)                                                                                40(50)                                 67      100       40      0      20(80)                                                                               100                                     68      100       10      20     20     0                                      69      100       40      0      20     0                                      70      100       40      20     0(20)  0                                      71      100.sup.c                                                                                60      0      0(20)  0                                      72       60       0       0      20     0                                      73      100      100      0      40(80)                                                                               100                                     74      100       80      0      20     0                                      75      100       60      0      0      0                                      76      100       60      0      0(20)  0                                      77      100      100      0      0      0                                      78       90       40      0      20     0                                      79       0.sup.d  0       20     0      0                                      80       20.sup.d                                                                                0       20     0      0                                      81      100       0       20     0      20                                     82      100       0       0      0      0                                      83      100      100      0      60(100)                                                                              100                                     84       10       0       0      0      0                                      85      100       30      0      0      20                                     86      100       30      20     0      80(100)                                87      100       40      40      0     40(50)                                 88      100       20      0      0      0                                      89      100       0       0      0     100                                     90      100       0       0      0      90                                     91      100.sup.a,c                                                                              0       40     0      0                                      92      100       50      0      0      90(100)                                93      100       0       0      0      0                                      94       0.sup.d  10      0      0      0                                      95      100      100      20     40(100)                                                                              100                                     96      100       30      0      0      0                                      97      100       0       20     0      0                                      98      100       0       0      0     100                                     99      100       60      0      40(80)                                                                               100                                    100      100      100      0      80(100)                                                                              100                                    101      100.sup.c                                                                                0       0      20     0                                     102      100       0       0      20     0(40)                                 103      100      100      0      0(60) 100                                    104      100       0       0(20)  0      40(100)                               105      100       0       40     0     100                                    106       80       0       60     0      0(100)                                107      100       0       0      0(40) 100                                    108      100       0       0      0      0                                     109      100       20      0      0(100)                                                                               100                                    110      100       70      0     100     90(100)                               111      100      100      0      0      0                                     112      100      100      20     20(40)                                                                                90(100)                               113      100      100      0     100    100                                    114      100       0       0      0      10                                    115      100      100      0      20(60)                                                                                90(100)                               116      100       10      0      0      0                                     117      100       10      0      40(80)                                                                               100                                    118      100       10      0      0      90(100)                               119      100       0       0      0      0                                     120      100       30      20     0      0                                     121      100      100      0      20(40)                                                                               100                                    122       70       20      0      0      20(50)                                123      100       0       0      0(100)                                                                               100                                    124      100      100      0      0      20(30)                                125      100       0       0      0      0                                     126      100       10      0      0      0                                     127      100       10      0      20     0                                     128      100       0       0      0      0                                     129      100       40      40(60)                                                                               100(80)                                                                                80(100)                               130      100       0       0      0(20) 100                                    131      100       0       0      0     100                                    132      100       0       0      20(40)                                                                                0                                     133      100       10      0      0      0                                     134      100       10      0      0      10(30)                                135      100       0       0      20(40)                                                                                60                                    136      100       70      0      20     30(50)                                137      100       10      0      40(60)                                                                                0                                     138      100       0       0      0      90(100)                               139      100       0       0      0(20)  0                                     140      100       0       0      20     0                                     141      100      100      0      20(100)                                                                              100                                    142      100       0       0      20     40                                    143       0.sup.d  0       0      20     0                                     144       0.sup.d  10.sup.a,c                                                                             20.sup.c                                                                              0      0                                     145       30.sup.c                                                                                0       0.sup.c                                                                               0      0                                     146      100       20      40(60)                                                                                0      0                                     147       0.sup.d  20.sup.d                                                                                20.sup.d                                                                             0.sup.d                                                                               0.sup.d                               148       60.sup.d                                                                                0       40     0      20(0)                                 149       20.sup.c                                                                                20.sup. a,c                                                                            0.sup.c                                                                               0      0                                     150       20.sup.c                                                                                0       0.sup.c                                                                               0      0                                     151       0        0       0      0      0                                     152      100       0       0      0      0                                     153      100       0       0      0      89(90)                                154      100       10      0      0      0                                     155       0.sup.d  30      0      0(20)  0                                     156       10.sup.c                                                                                0       0.sup.c                                                                               0      0                                     157       0.sup.d  10      20     0      0                                     158       20       0       0      0      0                                     159       10       0       0      0      0                                     160       20.sup.d                                                                                0       0      20     0                                     161       30       0       0      0(20)  0                                     162       70       20      0      40(60)                                                                                0                                     163       20       20      0      0(20)  0                                     164      100.sup.d                                                                                0       20     40     0                                     165       20.sup.c                                                                                10      0      0      0                                     166       10       10      0      0      0                                     167       30       0       0      0      0                                     168       10       40      0      0      0                                     169       0.sup.d  30      0      0      0                                     170       0.sup.d  10      0      0      0                                     171      100       40      0      0      0                                     172      100       0       0      0      0                                     173       60       30      20     0      0                                     174      100       0       0      0      80(100)                               175      100       0       0      0      0                                     176       0.sup.d  10      0      0      0                                     177      100       30      0      0      10                                    178      100       10      0      0      10                                    179       90       0       20     0      0                                     180      100       0       0      0      0                                     181      100       10      0      0      0                                     182      100       0       0      0      0                                     183       30       80      0      0(100)                                                                                0(100)                                184      100       10      0      0      0                                     185       30.sup.c                                                                                20.sup.a,c                                                                             0.sup.c                                                                               0      0                                     186       30.sup.c                                                                                10.sup.d                                                                               30.sup.d                                                                              20.sup.d                                                                              0.sup.d                               187      100       0       0      0(20)  0(10)                                 188      100.sup.c                                                                                0       0.sup.c                                                                               0      0                                     189      100.sup.c                                                                                0       20     0      0                                     190      100       0       0      0(40)  20(60)                                191       90       0       0      0      0                                     192       20       0       0      0      0                                     193      100       0       0      0      0                                     194      100       80      20     20(60)                                                                               100                                    195      100       80      0      80(100)                                                                              100                                    196      100       0       0      0     100                                    197      100       0       20     0(20) 100                                    198      100       0       0      20     90(100)                               199       20       10      0      20     30                                    200      100       0       0      0(20)  90                                    201      100       0       0(60)  0      20(30)                                202       40       20      0      40     0                                     203       60       0       20(60)                                                                                0      0                                     204       50       0       0      0      0                                     205      100       10      0      20    100                                    206      100       10      0      0     100                                    207       0.sup.d  20.sup.d                                                                               20.sup.d                                                                              0.sup.d                                                                               0(10).sup.d                           208      100       0       0      0(20) 100                                    209      100       10      0      60(20)                                                                               100                                    210       20.sup.c                                                                                10      40     0      0                                     211       20       10      0      0      0                                     212      100       0       0      0      90(100)                               213      100       0       40     0      0                                     214      100       0       0      0      40(60)                                215      100       10      0      0(20) 100                                    216      100       0       20     20     50(60)                                217      100       60      0      20    100                                    218       90       10      0      0      0                                     219       60.sup.c                                                                                0       0.sup.c                                                                               0      0                                     220      100       0       0      0     100                                    221       60       10      0      20     0                                     222      100.sup.c                                                                                10.sup.a,c                                                                             0.sup.c                                                                               0      0                                     223      100       10      0      40    100                                    224       40       10      20     0      0                                     225      100       20      0      0(20) 100                                    226      100       10      0      0      0                                     227      100       0       0      0      30(40)                                228      100       0       20     0(40) 100                                    229       60       20      0      0      0                                     230      100       50      0      60(80)                                                                               100                                    231       60       20      0      40     60                                    232      100       0       0      20     0                                     233      100       0       0      40     60                                    234      100       10      0      0     100                                    235      100       60      0     100    100                                    236      100       10      0      0      30                                    237      100       20      0      0      0                                     238       90       60      0      0      0                                     239      100       0       0      0      0                                     240       30       10      0      0       0                                    241      100       0       0      0      0                                     242       50       30      0      0      0                                     243       10       20      0      0      0                                     244      100       0       0      0      70(80)                                245      100       0       0      0      80(90)                                246      100       10      0      0      0                                     247      100       0       0      0      0                                     248      100       0       0      0      0                                     249      100       0       0      0      0                                     250       80       50      0      0      10                                    251      100       20      20     20(40)                                                                                60                                    252      100       0       0      0(20) 100                                    253      100       10      20(40)                                                                                0      20(30)                                254      100       0       0      0      0                                     255      100      100      0      0      0                                     256      100       0       0      0      0                                     257      100       0       0      20     20                                    258       40.sup.c                                                                                90      40    100     0                                     259      100       10      0      0      0                                     260      100       20      0       0     0                                     261       0.sup.d  10      0      0      0                                     262       60       0       0      0      0                                     263      100       30      0      20     40                                    264       80       0       80(100)                                                                               0      10(30)                                265       0.sup.c  10      0      0      0                                     266       0.sup.d  10      0      0      0                                     267      100       0       0      0      0                                     268       40       0       0      0      0                                     269      100       0       60(80)                                                                                0      0                                     270      100       0       0      20(40)                                                                                0                                     271      100       10      0      20(0)  70                                    272       40       10      0      0      0                                     273      100       0       40(100)                                                                               0      0                                     274      100       10      0      20     50(90)                                275       40.sup.c                                                                                30.sup.a,c                                                                             0.sup.c                                                                               0      0                                     276      100       10      20(60)                                                                                0      0                                     277      100       30      0      20     0                                     278       60       0       0      0      0                                     279      100       10      0      0      0                                     280      100       10      20(80)                                                                                0      0                                     281      100       0       0      0      0                                     282      100       30      0      0      0                                     283      100       0       0      0      0                                     284       90       50      0      0      0                                     285      100       50      0      0      0                                     286      100       0       0      0      0                                     287      100       10      0      0      0                                     288      100       0       0      0      0                                     289      100       40      0      20     0                                     290      100       50      0      0      0                                     291      100       30      0      0      80(90)                                292      100       10      0      0     100                                    293       20       30      20     0      0                                     294       0.sup.d  10.sup.a,c                                                                             0.sup.c                                                                               0      0                                     295      100      100      0      0      60(80)                                296      100       50      0      60(100)                                                                              100                                    297      100       40      0      0      0                                     298       80       30      0      0      0                                     299      100       20      0      0      0                                     300      100       0       0      0(20) 100                                    301      100       0       0      0      70(100)                               302      100       0       0      0      0                                     303      100       30      0      0      0                                     304       70       90      0      0      0                                     305      100       40      0      0      60(100)                               306      100       40      0      0      0                                     307      100       60      0      0      0                                     308       0.sup.d  40      0      0      0                                     309      100       60      0      0      0                                     310      100       40      0      0      0                                     311      100      100      0      40(60)                                                                                90(100)                               312      100       0       0      0      10                                    313      100       20      0      0      0                                     314      100       0       0      0      0                                     315      100       0       0      20(40)                                                                                0                                     316      100       0       0      20    100                                    317      100       20      0      0      80(100)                               318      100       20      0      0      90(100)                               319      100       20      0      0     100                                    320      100       0       0      40     0                                     321       80       0       0      --     --                                    322      100       0       0      --     --                                    323      100       20      0      --     --                                    324      100       20      0      --     --                                    325      100       10      0      --     --                                    326      100       30      0      --     --                                    327       30       30      0      --     --                                    328       0.sup.d  50      0      --     --                                    329      100       30      0      --     --                                    330      100       30      0      --     --                                    331      100       30      0      --     --                                    332      100       70      0      --     --                                    333       30       0       0      --     --                                    334      100       0       0      --     --                                    335       90       70       0     --     --                                    336      100       30      0      --     --                                    337       50.sup.c                                                                                30      0      --     --                                    338      100       40      0      --     --                                    339      100       0       20(80)                                                                                --     --                                    340      100       0       0      --     --                                    341      100      100      0      --     --                                    342      100       0       0      --     --                                    343      100       10      20(60)                                                                                --     --                                    344       0.sup.c  0       40     --     --                                    345       20       0       0      --     --                                    346       40.sup.c                                                                                10.sup.a,c                                                                             0.sup.c                                                                               --     --                                    347      100       20      0      --     --                                    348      100.sup.c                                                                                0       0.sup.c                                                                               --     --                                    349       60       0       0      --     --                                    350      100       20      0      --     --                                    351      100       0       0      --     --                                    352       50       20      0      --     --                                    353      100       0       0      --     --                                    354      100       30      0      --     --                                    355      100.sup.c                                                                                90      0      --     --                                    356       40.sup.c                                                                                0       0.sup.c                                                                               --     --                                    357      100       20      0      --     --                                    358      100       0       0      --     --                                    359      100       0       0      --     --                                    360       70.sup.c                                                                                0       0.sup.c                                                                               --     --                                    361      100       10      0      --     --                                    362      100       70      0      --     --                                    363      100       20      0      --     --                                    364      100       10      0      --     --                                    365      100       0       0      --     --                                    366      100       40      0      --     --                                    367      100       30      0      --     --                                    368      100       0       0      --     --                                    369      100       0       0      --     --                                    370       30       30      0      --     --                                    371      100       10      20     --     --                                    372       30       0       0      --     --                                    373       90       10      0      --     --                                    374      100       10      0      --     --                                    375      100.sup.d                                                                                10      0      --     --                                    376      100.sup.c                                                                                20      0      --     --                                    377      100       20      0      --     --                                    378      100       20      0      --     --                                    379      100       20      0      --     --                                    380      100       10      0      --     --                                    381      100       30      0      --     --                                    382      100       0       20     --     --                                    383      100       20       0     --     --                                    384       80       20      0      --     --                                    385      100      100      0      --     --                                    386      100       20      20     --     --                                    387      100       0       0      --     --                                    388      100       30      20(40)                                                                                --     --                                    389       0.sup.d  70      0      --     --                                    390      100       30      0      --     --                                    391      100       0       20(60)                                                                                --     --                                    392      100      100      0      --     --                                    393      100       20      0      --     --                                    394      100       0       0      --     --                                    395      100       70      0      --     --                                    396      100      100      0      --     --                                    397      100       0       0      --     --                                    398      100       40      0      --     --                                    399      100       0       0      --     --                                    400       90       0       0      --     --                                    401      100       70      0      --     --                                    402      100       40      0      --     --                                    403      100       0       0      --     --                                    404      100       20      20(40)                                                                                --     --                                    405      100       10      0      --     --                                    406      100       0       20     --     --                                    407      100       20      0      --     --                                    408       90       60      0      --     --                                    409       40       0       0      --     --                                    410      100       90      0      --     --                                    411      100       10      0      --     --                                    412       30       30      0      --     --                                    413      100       10      0      --     --                                    414       60       50      40     --     --                                    415       60       20      20(60)                                                                                --     --                                    416      100        30     0      --     --                                    417      100       20      0      --     --                                    418      100       0       20     --     --                                    419      100       10      0      --     --                                    420      100       0       40     --     --                                    421      100       10      0      --     --                                    422      100       0       0      --     --                                    423      100       0       0      --     --                                    424      100       10      0      --     --                                    425      100       70      0      --     --                                    426      100       0       0      --     --                                    427      100       20      0      --     --                                    428      100       10      20(80)                                                                                --     --                                    429      100       20      0      --     --                                    430      100       0       0      --     --                                    431       90       40      0      --     --                                    432      100       20      0      --      --                                   433      100       0       0      --     --                                    434      100       10      20     --     --                                    435      100       20      0      --     --                                    436       0.sup.d  30      0      --     --                                    437      100       10      0      --     --                                    438      100       40      0      --     --                                    439      100       0       0      --     --                                    440      100       20      0      --     --                                    441      100       20      0      --     --                                    442      100       30      0      --     --                                    443      100       20      0      --     --                                    444      100       0       0      --     --                                    445      100       20      0      --     --                                    446      100       20      20     --     --                                    447      100       20      0      --     --                                    448      100       20      0      --     --                                    449      100       20      0      --     --                                    450      100       20      0      --     --                                    451      100       50      0      --     --                                    452      100       30      0      --     --                                    453      100       30      0      --     --                                    454      100       0       0      --     --                                    455      100       50      0      --     --                                    456      100       20      0      --     --                                    457      100       50      0      --     --                                    458      100       0       0      --     --                                    459      100       0       20     --     --                                    460      100       0       0      --     --                                    461       0.sup.d  10.sup.a,c                                                                             0.sup.c                                                                               --     --                                    462       40       20      0      --     --                                    463       50       10      0      --     --                                    464      100       10      0      --     --                                    465       70       0        0     --     --                                    466      100       0       40     --     --                                    467      100       0       0      --     --                                    468      100       10      0      --     --                                    469       60.sup.c                                                                                20      0      --     --                                    470      100       10      0      --     --                                    471      100       10      0      --     --                                    472      100       0       0      --     --                                    473      100       20      0      --     --                                    474      100.sup.c                                                                                20      0      --     --                                    475       50.sup.c                                                                                0       0.sup.c                                                                               --     --                                    476      100       0       0      --     --                                    477      100       10      20     --     --                                    478      100       20      0      --     --                                    479      100       0       0      --     --                                    480      100       20      0      --     --                                    481      100       0       0       --    --                                    482      100       20      0      --     --                                    483      100       10      0      --     --                                    484      100       20      0      --     --                                    485      100       40      0      --     --                                    486      100       20      0      --     --                                    487      100       50      0      --     --                                    488      100       0       0      --     --                                    489      100       40      20     --     --                                    490      100       0       0      --     --                                    491       60       20      0      --     --                                    492      100       0       0      --     --                                    493      100       20      0      --     --                                    494      100       0       0      --     --                                    495      100       10      0      --     --                                    496      100       0       0      --     --                                    497      100       10      0      --     --                                    498      100       0       60(80)                                                                                --     --                                    499      100       40      0      --     --                                    500      100       10      0      --     --                                    501      100       30      0      --     --                                    502      100       10      20     --     --                                    503       90       30      0      --     --                                    504      100       40      0      --     --                                    505      100       30      20     --     --                                    506      100       0       0      --     --                                    507       60       20      0      --     --                                    508      100       0       0      --     --                                    509      100       70      0      --     --                                    510      100       10      0      --     --                                    511      100       10      0      --     --                                    512       90       20      0      --     --                                    513      100       10      0      --     --                                    514      100       30      0       --    --                                    515      100      100      0      --     --                                    516      100       10      0      --     --                                    517      100       10      0      --     --                                    518      100       30      0      --     --                                    519      100       10      0      --     --                                    520      100       30      0      --     --                                    521      100       50      0      --     --                                    522      100       10      0      --     --                                    523      100       10      0      --     --                                    524       90       30      0      --     --                                    525      100       30      0      --     --                                    526      100       10      0      --     --                                    527      100       0       0      --     --                                    528      100       0       0      --     --                                    529      100       10      0      --     --                                    530      100       10      0      --     --                                    531      100        10     0      --     --                                    532      100       20      0      --     --                                    533      100       0       0      --     --                                    534      100       10      0      --     --                                    535      100       0       0      --     --                                    536      100       10      0      --     --                                    537      100       0       0      --     --                                    538      100       20      0      --     --                                    539      100       0       0      --     --                                    540      100       10      0      --     --                                    541      100       0       0      --     --                                    542      100       0       0      --     --                                    543      100       0       0      --     --                                    544      100       0       0      --     --                                    545      100       0       0      --     --                                    546      100       0       0      --     --                                    547      100       0       0      --     --                                    548      100       30      20     --     --                                    549      100       30      0      --     --                                    550      100       40      0      --     --                                    551      100       0       0      --     --                                    552      100       30      20     --     --                                    553      100       40      0      --     --                                    554      100       20      0      --     --                                    555      100       20      0      --     --                                    556      100       10      0      --     --                                    557       30       30      0      --     --                                    558      100       20      0      --     --                                    559      100       50      0      --     --                                    560       90       0       0      --     --                                    561      100       30      20     --     --                                    562      100       0       0      --     --                                    563      100       10      0      --     --                                    564      100       0        0     --     --                                    565      100       0       0      --     --                                    566       40       70      0      --     --                                    567      100       40      20     --     --                                    568      100       0       0      --     --                                    569      100       20      0      --     --                                    570      100       10      0      --     --                                    571      100       50      0      --     --                                    572      100       80      0      --     --                                    573      100       20      0      --     --                                    574      100       0       0      --     --                                    575      100       0       20     --     --                                    576      100       20      0      --     --                                    577      100       0       0      --     --                                    578      100       40      0      --     --                                    579      100       40      0      --     --                                    580      100       0       0      --     --                                    581      100       0       0      --     --                                    582      100       0       0      --     --                                    583      100       30      0      --     --                                    584      100       0       0      --     --                                    585      100       0       0      --     --                                    586      100       0       0      --     --                                    587      100       10      0      --     --                                    588      100       40      0      --     --                                    589      100       40      0      --     --                                    590      100       30      0      --     --                                    591      100       0       0      --     --                                    592      100       40      0      --     --                                    593      100       40      0      --     --                                    594      100       10      0      --     --                                    595      100       10      20     --     --                                    596      100       80      0      --     --                                    597      100       40      0      --     --                                    598      100       10      20     --     --                                    599      100       40      0      --     --                                    600      100       30      0      --     --                                    601      100       10      0      --     --                                    602      100       10      0      --     --                                    603      100       20      0      --     --                                    604      100       10      0      --     --                                    605      100       20      20(80)                                                                                --     --                                    606       80.sup.d                                                                                20      0      --     --                                    607       80       10      0      --     --                                    608      100       30      0      --     --                                    609      100       20      0      --     --                                    610       0.sup.d  20      0      --     --                                    611       30       30      0      --     --                                    612       0(30).sup.a                                                                             20      0      --     --                                    613       0(70).sup.a                                                                             50      0      --     --                                    614       10       20      0      --     --                                    615      100       20      0      --     --                                    616      100       0       0      --     --                                    617      100       10      0      --     --                                    618      100       10      0      --     --                                    619      100       0       0      --     --                                    620       70       30      20(40)                                                                                --     --                                    621      100       10      0      --     --                                    622      100       70      0      60(100)                                                                              100                                    623      100       0       0      0      20(50)                                624      100       80      0      0      80(100)                               625      100       10      20     --     --                                    626      100       90      0      --     --                                    627      100       0       0      --     --                                    628      100       40      0      --     --                                    629      100       0       0      --     --                                    630      100       0       0       --    --                                    631      100       0       0      --     --                                    632      100       30      0      --     --                                    633      100       10      0      --     --                                    634      100       90      0      --     --                                    635       0.sup.d 100      0      0      0                                     636       80.sup.d                                                                               100      0      0      0                                     637      100      100      0      20(60)                                                                               100                                    638      100       10      20     --     --                                    639       10       20      0      --     --                                    640      100       80      0      0      0                                     641      100       30      0      --     --                                    642      100      100      0      --     --                                    643      100       20      0      --     --                                    644      100       40      0      --     --                                    645      100       20      0      --     --                                    646      100       0       0      20    100                                    647      100       60      20     20     40(60)                                648       70      100      0      80(20)                                                                                40(100)                               649      100       40      0      40     0(80)                                 650      100.sup.c                                                                                10      0      0(40)  0(20)                                 651       90       60      40     80(60)                                                                                0(20)                                 652       20       10      0      0(40)  40(60)                                653       0.sup.d  0       0      0(20)  0                                     654       70      100      0      20(40)                                                                                0                                     655       80       70      0      40(100)                                                                               40(80)                                656      100       0       0      0     100                                    657       30       0       0      0      0                                     658       40.sup.c                                                                                90      20     80(100)                                                                               0                                     659       30.sup.c                                                                                80      0      0(80)  0                                     660       80.sup.c                                                                                70      0      0      0                                     661      100       20      0      0      0                                     662       70       40      20     0      0                                     663      100       0       0      --     --                                    664      100.sup.c                                                                                0       0      0      0                                     665       60       30      20(40)                                                                                0(20)  0                                     666      100       0       0       --    --                                    667      100       0       0      --     --                                    668       60.sup.d                                                                                20      0      --     --                                    669       20.sup.d                                                                                30      0      --     --                                    670       90       40      0      --     --                                    671      100       30      0      --     --                                    672      100      100      0      --     --                                    673       20       40      0      --     --                                    674      100       50      80     --     --                                    675      100       30      0      --     --                                    676      100.sup.c                                                                                80      0      --     --                                    677       70.sup.c                                                                                40      0      --     --                                    678       50       30      0      --     --                                    679      100       30      0      --     --                                    680      100       10      0      --     --                                    681      100      100      0      --     --                                    682       10       40      0      --     --                                    683      100       0       0      0      20                                    684       20.sup.a                                                                               100.sup.a                                                                               0      --     --                                    685       10.sup.c                                                                                10.sup.a,c                                                                             40     --     --                                    686       20.sup.c                                                                                0.sup.a,c                                                                              0      --     --                                    687       0.sup.d  30.sup.a,c                                                                             0      --     --                                    688      100      100      0      60(100)                                                                              100                                    689       90       50      0      40(100)                                                                               0(20)                                 690       0.sup.d  10.sup.d                                                                               0.sup.d                                                                               0.sup.d                                                                               0.sup.d                               691       30.sup.c                                                                                10      0      0      0                                     692       80       0.sup.a                                                                                0      --     --                                    693       0.sup.d  20      0      0      0                                     694       80       80      40     0      0                                     695       60.sup.d                                                                                30      0      0      0                                     696       0.sup.d  40      20     20     0                                     697       20.sup.c                                                                                0       0      0      0                                     698      100       0        20    0     100                                    699      100      100      0      60(100)                                                                               90                                    700       0.sup.d 100.sup.a,c                                                                             0      0      0                                     701       90.sup.c                                                                                10      20     40(20)                                                                                0                                     702       0.sup.d 100      0      0      0                                     703       10.sup.a                                                                                0.sup.a                                                                                0      --     --                                    704       0.sup.d  30      0      --     --                                    705       80       0       0      --     --                                    706       30       30      20     --     --                                    707      100       40      0      --     --                                    708      100       10      0      --     --                                    709       80.sup.d                                                                               100      20(40)                                                                                --     --                                    710      100       30      0      --     --                                    711      100       30      0      --     --                                    712      100       20      0      --     --                                    713      100       60      0      --     --                                    714      100       40      0      --     --                                    715      100       20      0      --     --                                    716      100       0       0      --     --                                    717      100       40      0      --     --                                    718       10.sup.c                                                                                70      0      --     --                                    719       0.sup.d  20      0      --     --                                    720      100       0       0      --     --                                    721      100       30      0      --     --                                    722       50       0       40     0      0                                     723      100       80      40     60(100)                                                                               90(100)                               724       90       10      0      0(20)  0                                     725      100       0       0      0      0                                     726      100       30      0      20    100                                    727      100       30      0     100    100                                    728       0.sup.d  0.sup.d                                                                                20.sup.d                                                                              0.sup.d                                                                               0.sup.d                               729      100       70      0     100    100                                    730      100       0       0      0      10                                    731       70       50      0      40(20)                                                                                50(60)                                732      100       0       20      0    100                                    733      100       50      0      0      80(100)                               734       10.sup.c                                                                                0       20     0      0                                     735      100       10      0      20     80(100)                               736      100       0       0      0      90(100)                               737      100       0       0      0      0                                     738      100       80      0      80    100                                    739      100       20      0      0      0                                     740       30       30      0      0      0                                     741      100       0       0      --     0                                     742      100       0       0      --     0                                     743      100       40      0      --     0                                     744      100       20      0      --     0                                     745      100       10      0      --     0                                     746      100       0       0      --     0                                     747       70       20      0      --     0                                     748      100.sup.d                                                                               100.sup.d                                                                               0.sup.d                                                                               0.sup.d                                                                               0(10).sup.d                           749      100       0       0      --     0                                     750       20       30      0      --     0                                     751      100       0       20     --     0                                     752       10       20      0      --     0                                     753      100       20      0      --     0                                     754      100       70      0      --     0                                     755      100       10      0      --     0                                     756      100       0       0      --     --                                    757      100       0       0      --     --                                    758      100      100      0      --     --                                    759      100       10      0      --     --                                    760      100.sup.c                                                                                40      20(40)                                                                                --     --                                    761       0.sup.d  90      0      --     --                                    762      100       40      0      --     --                                    763      100       90      0      --     --                                    764       80       80      0      0      50(90)                                765      100       10      0      40(100)                                                                              100                                    766      100       20      20     0(20) 100                                    767      100       0       0      0      0                                     768       50       10      40      0     0                                     769      100       20      20     0(20)  0                                     770       50       30      20     0(20)  0                                     771       50.sup.c                                                                                0       0      0(20)  0                                     772       90       10      0      0(20)  0                                     773       20       40      0      0      0                                     774      100       0       20     20     90                                    775      100       30      0      0      20(30)                                776       40       0       0      0      0                                     777       60.sup.c                                                                                30.sup.a,c                                                                             20.sup.c                                                                              0      0                                     778      100       10      0      0      0                                     779       90       20      0      0      0                                     780      100       0       0      0      0                                     781      100       80      0      40(100)                                                                              100                                    782       40       70      0      0(20)  40                                    783      100       10      0      0      10                                    784      100       30      0      0      0                                     785      100       20      0      40(0)  80(100)                               786       60       0       0      0      0                                     787       30       30      0      --     --                                    788       70       30      0      --     --                                    789      100       0       0      --     --                                    790      100       90      0      --     --                                    791       20.sup.c                                                                                10      0      0      0                                     792       0.sup.d  10.sup.a,c                                                                             .sup. 0.sup.c                                                                         0      0                                     793       20       0       0      --     --                                    794       0.sup.d  10      0      0      0                                     795      100       30      0      --     --                                    796      100       30      0      --     --                                    797      100       0       0      --     --                                    798      100       10      0      --     --                                    799       10.sup.a                                                                                0.sup.a                                                                                0      0      0                                     800       30.sup.a                                                                                30.sup.a                                                                               20     0      0                                     801       20.sup.c                                                                                10      0      0      0                                     802      100       40      0      80     80(100)                               803      100       60      0      0      0                                     804      100       30      0      0      0                                     805      100       30      0      --     --                                    806      100       20      0      --     --                                    807      100       0       0      --     --                                    808      100       20      0      --     --                                    809      100       0       0      --     --                                    810      100       50      0      --     --                                    811       50       0       0      --     --                                    812      100       0       60     --     --                                    813      100       0       0      --     --                                    814      100       20      20     --     --                                    815      100       0       0      --     --                                    816      100       0       0      --     --                                    817      100       30      0      --     --                                    818      100       40      0      --     --                                    819       30       10      0      0(20)  0                                     820      100       0.sup.a                                                                                0       0(20)                                                                                0                                     821      100.sup.a                                                                                70      0      0(20)  0                                     822      100.sup.a                                                                               100      40(100)                                                                               0(100)                                                                               100                                    823      100.sup.a                                                                                0.sup.a                                                                                0      --     --                                    824       0.sup.d  10      0      --     --                                    825      100.sup.a                                                                                30      0      --     --                                    826      100.sup.a                                                                                0.sup.a                                                                                0      --     --                                    827       60       10.sup.a                                                                               0      --     --                                    828       0.sup.a  0.sup.a                                                                                20     --     --                                    829      100      100      0      20(80)                                                                                80(90)                                830       0        10      0      0      20                                    831      100       0       0      0      0                                     832      100       0       0      0      0                                     833       60       0       0      0      20                                    834       0        0       40     0      0                                     835      100       90      0      60    100                                    836       0        50      0      0      0                                     837       0        0       20     0      0                                     838       0       100      0      0      70                                    839      100       40      0      0     100                                    840       0        0       0      0      0                                     841       0        0       20     0(20)  0                                     842       10       20      0      0(20)  0                                     843       40       50      0      20(60)                                                                                50(90)                                844       0        10      0      0      0                                     845       70       10      0      0(40)  0                                     846       40       0       40     20     0                                     847       0        30      0      20     0                                     848       40       30      20     0(60)  20(80)                                849       0        10      40     0      0                                     850       10       0       0      0      0                                     851       0        0       0      20     0                                     852       0        0       0      20(40)                                                                                0                                     853       0        0       0      0      0                                     854       0        60      0      60     0                                     855       0        90      0      0      0                                     856      100       0        0     0      0                                     857       50       20      20     0(20)  0                                     858       0        10      0      0      0                                     859       0        60      0      60     0                                     860       0        10      0      0      0                                     861       0        10      0      0      0                                     862       0        10      0      0(40)  0                                     863       0        20      0      0      0                                     864       40       0       0      0      0                                     865      100       50      0      0      0(20)                                 866       0       100      0      0      0                                     867       0       100      0      0      0                                     868       10       0       20     0      0                                     869       0        0       0      40     0                                     870      100       10      0      0      80(90)                                871       0        0       0      0      0                                     872       0        10      20     0      0                                     873       0        20      0      --     --                                    874      100       0       0      --      --                                   875       20       20      0      --     --                                    876      100       20      0      --     --                                    877       80       10      0      --     --                                    878      100       10      0      --     --                                    879       30       30      20     --     --                                    880      100       10      --     --     --                                    881       80       80      40     0      0                                     882      100       0       0      --     --                                    883       90       50      0      0(20)  40(100)                               884       0        0       0      --     --                                    885       90       30      0      --     --                                    886      100       10      0      --     --                                    887      100      100      0      --     --                                    888       30      100      0      --     --                                    889      100       40      0      --     --                                    890      100       70      0      --     --                                    891      100        20     0      --     --                                    892      100       30      20     --     --                                    893       0        40      0      --     --                                    894      100       0       0      --     --                                    895      100       20      0      --     --                                    896      100       30      0      --     --                                    897      100       0       0      --     --                                    898      100       30      0      --     --                                    899      100       10      0      --     --                                    900      100       0       0      --     --                                    901      100       10      0      --     --                                    902      100       0       0      --     --                                    903      100       30      0      --     --                                    904      100       0       0      --     --                                    905      100       0       0      --     --                                    906       0        10      0      --     --                                    907      100       0       0      --     --                                    908      100       30      40     --     --                                    909      100       30      0      --     --                                    910      100       50      0      --     --                                    911      100       0       0      --     --                                    912      100       10      0      --     --                                    913      100       0       0      --     --                                    914       0        0       0      0      0                                     915       90       10      0      0      0                                     916       0        0       0      0      0                                     917       0        0       20     0      0                                     918       0        0       0      0      0                                     919      100       40      20     0(20)  0                                     920       0        0       0      0      0                                     921       0        90      20     20     0                                     922       0        0       0(40)  0      0                                     923       0        30      0      --     --                                    924       0.sup.a  10.sup.a                                                                               0      --     --                                    925       --       --      --     --     --                                    926       0       100      20     0      60(100)                               927       0        0       0      0      20                                    928       20       30      0      0      20                                    929       0        60      0      0      0(20)                                 930       0        80      0      0      0                                     931       0       100      0      20(20)                                                                                20                                    932      100       40      0      40     0(20)                                 933       0        0       --     --     --                                    934      100      100      0      20     0                                     935       0        0       0      --     --                                    936       0        40      0      0      40                                    937       0        10      0      0      40                                    938       0        0       0      0      20                                    939       0        0       0      0      0                                     940       10       10      --     --     --                                    941       0        10      --     --     --                                    942       0        0       --     --     --                                    943       0        0       0      --     --                                    944       0        0       --     --     --                                    945       0        0       0      0      0                                     946       0        20      --     --     --                                    947       0        20      0      --     --                                    948       0        20      --     --     --                                    949       0        10      0      0      20                                    950       0        0       0      0      0                                     951       0        0       0      0      20(40)                                952       0        20      0      0      0                                     953       0        0       0      --     --                                    954       0        0       20     0      0                                     955       0        0       20     0      20(40)                                956       40       10      0(20)  0      0                                     957       40       60      0      0      0                                     958       0        0       0      0      0                                     959       0        0       0      0      20                                    960       0        0       0      0      0                                     961       0       100      40     0(20)  0                                     962       --       --      --     --     --                                    963       0        50      0      20     0                                     964       20      100      0      20     0                                     965       0        60      60     20(40)                                                                                0                                     966       0.sup.a  0.sup.a                                                                                0      --     --                                    967       0.sup.a  0.sup.a                                                                                0      --     --                                    968       0        30      0      0      20                                    969       0        --      --     --     --                                    970       0        --      --     --     --                                    971       0        --      --     --     --                                    972       0        --      --     --     --                                    973       0        --      --     --     --                                    974       0        --      --     --     --                                    975       0        --      --     --     --                                    976       10       --      --     --     --                                    977       0        --      --     --     --                                    978       60       --      --     --     --                                    979      100(80)   0(20)   0      --     --                                    980      100       0(30)   0      --     --                                    981      100       0       0      --     --                                    982      100       10(40)  0      --     --                                    983       0(30)    10(20)  0      --     --                                    984       30       10      0      --     --                                    985       0        20      0      --     --                                    986       0        0       0      --     --                                    987       0        0       0      --     --                                    988       0        0       0      --     --                                    989       0        0       0      --     --                                    990       0        30      0      --     --                                    991       0        0       0      --     --                                    992       0        0       0      --     --                                    993       0        0       0      --     --                                    994       0        0       0      --     --                                    995       0        0       0      --     --                                    996       20       20      0      --     --                                    997       0        30      0      --     --                                    998       0        0       0      --     --                                    999       0        0       0      --     --                                    1000      0        0       0      --     --                                    1001      0        10      0      --     --                                    1002      0        0       20     --     --                                    1003      0        10      0      --     --                                    1004      0        0       0      --     --                                    1005      0        --      --     --     --                                    1006      0        --      --     --     --                                    1007     100       0       0      --     --                                    1008      0        20      0      --     --                                    1009      0        30      0      --     --                                    1010      0        20      0      --     --                                    1011      0        0       0      --     --                                    1012      0        0       0      --     --                                    1013      0        40      0      --     --                                    1014      0        0       20     --     --                                    1015      0        10      0      --     --                                    1016     100       0       0      --     --                                    1017     100       40      0      --     --                                    1018      10       0       20     --     --                                    ______________________________________                                          .sup.a 48 hour observation                                                     .sup.b Not tested                                                              .sup.c Tested at 1200 ppm                                                      .sup.d Tested at 2400 ppm                                                

Not all compounds were tested by soil application. The results of the compounds tested are reported.

It should be understood that the instant specification and examples are set forth by way of illustration and not limitation, and that various modifications and changes may be made without departing from the spirit and scope of the present invention as defined by the appended claims. 

We claim:
 1. A compound of the formula ##STR27## wherein R_(a) is unsubstituted phenyl or substituted phenyl having from one to two substituents independently selected from (C₁ -C₆)alkyl and halo;R_(b) is unsubstituted phenyl or substituted phenyl having form one to two substituents independently selected from halo; nitro and (C₁ -C₆)alkyl; and R_(c) is halo(C₂ -C₆)alkyl.
 2. A compound of the formula ##STR28## wherein R_(a) is unsubstituted phenyl or substituted phenyl having from one to two substituents independently selected from (C₁ 1-C₆)alkyl and halo;R_(b) is unsubstituted phenyl or substituted phenyl having from one to two substituents independently selected from halo; nitro and (C₁ -C₆)alkyl; and R_(c) is halo(C₂ -C₆)alkyl; provided when R_(c) is CH₂ CF₃, R_(a) and R_(b) are not both 3,4-dichlorophenyl.
 3. The compound of claim 2 wherein R_(c) is CH(CH₃)CF₃ or CH₂ CF₃.
 4. The compound of claim 2 wherein R_(a) is phenyl, chlorophenyl dichlorophenyl or dimethylphenyl; R_(b) is phenyl, chlorophenyl, dichlorophenyl, dimethylphenyl or methylnitrophenyl.
 5. The compound of claim 4 wherein R_(c) is CH(CH₃)CF₃ or CH₂ CF₃.
 6. The compound of claim 4 wherein R_(a) is phenyl, 4-chlorophenyl, 3,4-dichlorophenyl or 2,3-dimethylphenyl; R_(b) is phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dimethylphenyl or 2-nitro-5-methylphenyl.
 7. The compound of claim 6 wherein R_(c) is CH(CH₃)CF₃ or CH₂ CF₃.
 8. The compound of claim 7 wherein R_(a) is 2,3-dimethylphenyl, R_(c) is CH(CH₃)CF₃ and R_(b) is 2,4-dichlorophenyl, 3,5-dimethylphenyl or 2-nitro-5-methylphenyl.
 9. The compound of claim 7 wherein R_(a) and R_(b) are phenyl.
 10. The compound of claim 7 wherein R_(a) and R_(b) are 4-chlorophenyl and R_(c) is CH₂ CF₃. 